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European	Journal	of	Chemistry	5	(2)	(2014)	260‐262	

	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2014	Eurjchem	Publishing	‐	Printed	in	the	USA	

http://dx.doi.org/10.5155/eurjchem.5.2.260‐262.992	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Synthesis	and	characterization	of	new	fatty	Schiff	base	ethers	of		
4‐((pyridin‐3‐ylmethylimino)methyl)phenol	

Mohini	Yarra,	Badari	Narayana	Prasad	Rachapudi	and	Sri	Lakshmi	Karuna	Mallampalli	*	

Centre	for	Lipid	Research,	Council	of	Scientific	and	Industrial	Research,	Indian	Institute	of	Chemical	Technology,	Hyderabad,	500007,	India	

*Corresponding	author	at:	Centre	for	Lipid	Research,	Council	for	Scientific	Industrial	Research‐Indian	Institute	of	Chemical	Technology,	Hyderabad,	500007,	India.		
Tel.:	+91.40.27193179.	Fax:	+91.40.27193370.	E‐mail	address:	karuna@iict.res.in	(S.L.K.	Mallampalli).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT	

	
DOI:	10.5155/eurjchem.5.2.260‐262.992	

Received:	06	December	2013	
Received	in	revised	form:	18	January	2014	
Accepted:	19	January	2014	
Online:	30	June	2014	

KEYWORDS	

	 A	 series	 of	 ten	 new	 Schiff	 base	 ethers	were	 synthesized	 by	 etherification	 of	 Schiff	 base‐{4‐
(pyridine‐3‐methylimino)	methyl	phenol}	with	fatty	alkyl	bromides	of	different	chain	lengths
(C4‐C18)	 in	 the	presence	of	base	with	80‐85%	isolated	yields.	All	 the	synthesized	Schiff	base
ethers	 (2a‐j)	 were	 characterized	 by	 FT‐IR,	 1H	 NMR,	 13C	 NMR	 and	 Mass	 spectral	 studies.
Presence	 of	 a	 characteristic	peak	 for	 ether	 linkage,	C‐O	at	 1039	 cm‐1	 in	 IR	 spectra;	 a	 triplet
around	7.67	ppm	in	1H	NMR	and	a	characteristic	peak	around	69.7	in	case	of		13C	NMR	further
confirmed	 the	 structures	 of	 Schiff	 base	 ethers.	 The	 structure	 of	 all	 the	 compounds	 were
further	confirmed	by	their	characteristic	molecular	ion	peaks	in	ESI‐MS.	

Synthesis	
Schiff	base	
Etherification	
Schiff	base	ether	
Pyridine	derivatives		
Fatty	alkyl	bromides	

	
1.	Introduction	
	

Schiff	 bases	 are	 compounds	 containing	 imine	 or	
azomethine	 moiety,	 a	 nitrogen	 analogue	 of	 an	 aldehyde	 or	 a	
ketone,	 where	 the	 carbonyl	 group	 (C=O)	 is	 replaced	 by	 an	
imine	 (or)	 azomethine	 group.	 Schiff	 bases	 are	 organic	
compounds	used	as	pigments	and	dyes,	catalysts,	intermediates	
in	 organic	 synthesis	 and	 as	 polymer	 stabilizers	 [1].	 The	
azomethine	 group	 present	 in	 the	 molecules	 exhibits	 many	
biological	activities	[2‐4].	Literature	survey	revealed	that,	most	
of	the	Schiff	bases	exhibit	wide	range	of	biological	activities	like	
anti‐fungal,	anti‐bacterial,	anti‐malarial,	anti‐inflammatory	and	
antipyretic	 properties	 [5‐10].	 Similarly,	 fatty	 acids	 and	
derivatives	 showed	 biological	 activities	 like	 antimicrobial	
[11,12],	 antifungal	 [13],	 and	 pesticidal	 activities	 [14]	 and	 the	
presence	 of	 ether	 bond	 linked	 to	 a	 lipid	 molecule	 further	
increases	 the	 biological	 activity	 [15].	 The	 existence	 of	 ether	
bond	 increases	 the	 resistance	of	 a	molecule	 to	hydrolysis	 and	
forms	 chemically	 stable	 bond.	 Keeping	 this	 in	 view,	 in	 the	
present	 study,	we	 focussed	 on	 the	 synthesis	 of	 a	 homologous	
series	 of	 ten	 novel	 Schiff	 base	 ethers	 by	 the	 etherification	 of	
Schiff	base‐4‐((pyridin‐3‐ylmethylimino)methyl)phenol.	
	
2.	Experimental	
	
2.1.	Instrumentation	

	

1H	and	13C	NMR	spectra	were	recorded	on	AVANCE	300	and	
500	 MHz	 and	 75	 MHz,	 respectively	 in	 CDCl3	 and	 DMSO‐d6.	
Chemical	 shifts	 relative	 to	 TMS	 as	 internal	 standards	 were	
given	 as	 δ	 values	 in	 ppm	 while	 the	 coupling	 constants	 were	
measured	 by	 J	 values.	 The	 melting	 point	 was	 determined	
through	 open	 capillary	 tubes	which	 are	 uncorrected.	 Infrared	
(IR)	 spectra	 were	 obtained	 on	 a	 1600	 FT‐IR	 Perkin‐Elmer	
Spectrometer	 (Norwalk,	 CT)	 with	 a	 liquid	 film	 between	 NaCl	
cells.	 Mass	 spectrometry	 was	 recorded	 by	 electron	 spray	
ionization	(ESI)	on	Shimadzu	LC/MS	instrument.	
	
2.2.	General	procedure	for	the	synthesis	of	Schiff	base													
4‐((pyridin‐3‐ylmethylimino)methyl)phenol	(1)	
	

Schiff	base	(1)	{4‐(pyridine‐3‐methylimino)	methyl	phenol}	
was	prepared	by	the	condensation	of	4‐hydroxy	benzaldehyde	
(2	 mmol)	 and	 3‐aminomethyl	 pyridine	 (2	 mmol)	 in	 absolute	
ethanol	 for	 6	 h	 at	 80‐85	 °C	 (Scheme	 1)	 which	 yielded	 Schiff	
base	[16].	C13H12N2O.	Yield:	80%.	M.p.:	143.6	°C.	1H	NMR	(300	
MHz	,	DMSO‐d6,	δ,	ppm):	4.72	(s,	2H,	N‐CH2‐),	6.79	(d,	2H,	J	=	8.4	
Hz,	Ar‐H),	7.26	(dd,	1H,	J	=	7.9	Hz,	Ar‐H),	7.57	(d,	2H,	J	=	7.7	Hz,	
Ar‐H),	7.66	(d,	1H,	J	=	3.5	Hz,	Ar‐H),	8.30	(s,	1H,	Ar‐H),	8.42	(d,	
1H,	J	=	4.7	Hz,	Ar‐H),	8.52	(s,	1H,	CH=N),	9.6	(s,	1H,	OH).		

	
	



Yarra	et	al.	/	European	Journal	of	Chemistry	5	(2)	(2014)	260‐262	 261	
 

	

	
	

R	=	butyl	(2a),	pentyl	(2b),	hexyl	(2c),	heptyl	(2d),	octyl	(2e),	
decyl	(2f),	dodecyl	(2g),	tetradecyl	(2h),	hexadecyl	(2i),	octadecyl	(2j)	

Scheme	1	
	
	

13C	NMR	 (75	MHz,	DMSO‐d6,	 δ,	 ppm):	 60.08	 (‐CH2‐N),	 114.51,	
122.28,	126.13,	128.74,	130.90,	134.43,	146.76,	147.85,	159.15	
(Aromatic),	 161.02	 (‐CH=N).	 MS/ESI	 (m/z):	 Calcd:	 212	 [M+],	
Found	213.2	[M+1].	
	
2.2.	Typical	procedure	for	the	synthesis	of	compound	2a‐j	
	

N‐(4‐butoxybenzylidene)‐1‐(pyridin‐3‐yl)methanamine	
was	synthesized	by	etherification	of	Schiff	base	1	with	1‐bromo	
butane	 taken	 in	 equimolar	 ratios	 (Scheme	 1).	 A	 solution	 of	
Schiff	 base	 (0.40	 g,	 2	 mmol)	 and	 1‐bromo	 butane	 (0.27	 g,	 2	
mmol)	 and	 little	 excess	 amount	 of	 base,	 potassium	 carbonate	
(2.76	g,	10	mmol)	was	dissolved	in	50	mL	dry	acetone	under	N2	
atmosphere	 and	 the	 contents	 were	 refluxed	 for	 12	 h	 stirring	
magnetically.	The	progress	of	the	reaction	was	monitored	using	
thin	 layer	 chromatography	 eluted	 with	 the	 solvent	 CHCl3:	
MeOH	(95:5,	v:v).	The	reaction	was	cooled	to	45	°C,	filtered	off	
the	by‐product	and	washed	with	20	mL	distilled	acetone.	The	
acetone	layer	was	concentrated,	dissolved	in	ethyl	acetate	and	
washed	 the	 product	with	 aqueous	 sodium	 bicarbonate	 (3×50	
mL)	solution.	The	organic	layer	was	separated,	passed	through	
anhydrous	 sodium	 sulphate	 and	 concentrated	 to	 obtain	 the	
crude	 N‐(4‐butoxybenzylidene)‐1‐(pyridin‐3‐yl)methanamine.	
The	crude	product	was	extracted	with	hexane	and	acetonitrile,	
where	the	pure	product	goes	into	the	hexane	layer.	The	hexane	
layer	 was	 concentrated	 to	 yield	 N‐(4‐butoxybenzylidene)‐1‐
(pyridin‐3‐yl)methanamine.	

Similarly	 all	 the	 Schiff	 base	 ethers,	 (4‐alkyloxy‐
benzylidene)‐pyridin‐3‐ylmethyl	 amine	 (2b‐j)	 were	 prepared	
following	 the	 above	 procedure	 (Scheme	 1).	 The	 synthesized	
Schiff	 base	 ethers	were	 characterized	 by	 FT‐IR,	 1H	 NMR,	 13	 C	
NMR	and	Mass	spectral	studies.		

N‐(4‐Butoxybenzylidene)‐1‐(pyridin‐3‐yl)methanamine	 (2a):	
Yield:	80%	(C17H20N2O).	FT‐IR	(νmax,	cm‐1):	2890	(C‐H	aliphatic),	
1625	(C=N),	1510	(C=C),	1039	(C‐O).	1H	NMR	(500	MHz,	CDCl3,	
δ,	ppm):	0.93	(t,	3H,	J=	6.9	Hz,	‐CH3),	1.43	(m,	2H,	CH3‐CH2‐	CH2‐
),	1.81	(quint,	2H,	‐CH2‐CH2‐O),	3.99	(t,	2H,	J	=	6.9	Hz,	 ‐CH2‐O),	
4.75	(s,	2H,	‐CH2‐N=CH‐),	6.92	(d,	2H,	J	=	8.8	Hz,	Ar‐H),	7.28	(d,	
1H,	J	=	6.8	Hz,	Ar‐H),	7.67	(d,	1H,	J	=	7.8	Hz,	Ar‐H),	7.72	(d,	2H,	J	
=	8.8	Hz,	Ar‐H),	8.31	(s,	1H,	Ar‐H),	8.46	(dd,	1H,	J	=	4.9	Hz,	Ar‐
H),	8.52	(s,	1H,	CH=N).	13C	NMR	(75	MHz,	CDCl3,	δ,	ppm):	14.15,	
24.52,	 25.25	 (Methylene	 carbons),	 61.10	 (‐CH2‐N),	 69.70	 (‐O‐
CH2‐CH2‐),	 114.52,	 123.52,	 129.52,	 131.5,	 135.52,	 136.18,	
148.21,	 149.31,	 161.55	 (Aromatic	 carbons),	 162.28	 (‐CH=N).	
MS/ESI	(m/z):	Calcd:	268	[M+],	Found	269	[M+1].	

N‐(4‐(Pentyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methanamine	
(2b):	 Yield:	 83%	 (C18H22N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2895	 (C‐H	
aliphatic),	 1604	 (C=N),	1540	 (C=C),	1039	 (C‐O).	 1H	NMR	 (500	
MHz	,	CDCl3,	δ,	ppm):	0.93	(t,	3H,	J	=	6.9	Hz,	‐CH3),	1.42	(m,	4H,	
CH3‐(CH2)2‐),	 1.80	 (quint,	 2H,	 ‐CH2‐CH2‐O),	 3.99	 (t,	 2H,	 J	=	6.9	
Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.93	(d,	2H,	J	=	8.8	Hz,	Ar‐
H),	7.27	(d,	1H,	J	=	6.7	Hz,		Ar‐H),	7.67	(d,	1H,	J	=	7.9	Hz,		Ar‐H),	
7.71	(d,	2H,	J	=	8.8	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	8.50	(dd,	1H,	J	=	
4.9	Hz,		Ar‐H),	8.60	(s,	1H,	‐CH=N).	13C	NMR	(75	MHz,	CDCl3,	δ,	
ppm):	14.05,	23.58,	24.32,	25.78	(Methylene	carbons),	61.04	(‐
CH2‐N),	 69.71	 (‐O‐CH2‐CH2‐),	 114.51,	 123.32,	 128.52,	 132.6,	
135.18,	 135.54,	 148.22,	 149.29,	 161.45,	 162.08	 (Aromatic	
carbons),	 162.08	 (‐CH=N).	 MS/ESI	 (m/z):	 Calcd:	 282	 [M+],	
Found	283	[M+1].	

N‐(4‐(Hexyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methanamine	
(2c):	 Yield:	 80%	 (C19H24N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2850	 (C‐H	
aliphatic),	 1601	 (C=N),	1587	 (C=C),	1039	 (C‐O).	 1H	NMR	 (500	
MHz	,CDCl3,	δ,	ppm):	0.91	(t,	3H,	J	=	6.9	Hz,	‐CH3),	1.46	(m,	6H,	
CH3‐(CH2)3‐),	 1.80	 (quint,	 2H,	 ‐CH2‐CH2‐O),	 4.11	 (t,	 2H,	 J	=	6.9	
Hz,	‐CH2‐O),	4.75	(s,	2H,	‐CH2‐N=CH‐),	6.94	(d,	2H,	J	=	8.8	Hz,	Ar‐
H),	7.29	(d,	1H,	J	=	6.7	Hz,		Ar‐H),	7.67	(d,	1H,	J	=	7.9	Hz,	Ar‐H),	
7.78	(d,	2H,	J	=	8.8	Hz,	Ar‐H),	8.40	(s,	1H,	Ar‐H),	8.48	(dd,	1H,		J	=	
4.7	Hz,	Ar‐H),	8.51	(s,	1H,	‐CH=N).	13C	NMR	(75	MHz,	CDCl3,	δ,	
ppm):	 14.05,	 23.58,	 24.32,	 25.78,	 30.21	 (Methylene	 carbons),	
61.10	 (‐CH2‐N),	 68.98	 (‐O‐CH2‐CH2‐),	 114.50,	 122.32,	 129.52,	
132.7,	 135.21,	 136.18,	 148.21,	 149.25,	 160.45	 (Aromatic	
carbons),	 161.92	 (‐CH=N).	 MS/ESI	 (m/z):	 Calcd:	 296	 [M+],	
Found	297	[M+1].	

N‐(4‐(Heptyloxy)	 benzylidene)‐1‐(pyridin‐3‐yl)methanamine	
(2d):	 Yield:	 81%	 (C20H26N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2980	 (C‐H	
aliphatic),	 1601	 (C=N),	1540	 (C=C),	1039	 (C‐O).	 1H	NMR	 (300	
MHz	,	CDCl3,	δ,	ppm):	0.90	(t,	3H,	J	=	6.9	Hz,	‐CH3),	1.46	(m,	8H,	
CH3‐(CH2)4‐	 ),	1.80	(quint,	2H,	 ‐CH2‐CH2‐O),	4.01	(t,	2H,	 J	=	6.6	
Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.93	(d,	2H,	J	=	8.8	Hz,	Ar‐
H),	7.28	(d,	1H,	J	=	6.8	Hz,		Ar‐H),	7.69	(d,	1H,	J	=	7.8	Hz,	Ar‐H),	
7.78	(d,	2H,	J	=	8.8	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	8.50	(dd,	1H,	J	=	
4.7	Hz,	Ar‐H),	8.53	(s,	1H,	‐CH=N	).	 3C	NMR	(75	MHz,	CDCl3,	δ,	
ppm):	 14.01,	 22.52,	 25.89,	 28.96,	 29.22,	 31.69	 (Methylene	
carbons),	62.17	(‐CH2‐N),	68.06	(‐O‐CH2‐CH2‐),	114.50,	123.31,	
128.48,	 129.78,	 132.6,	 135.44,	 148.26,	 149.29,	 160.55,	 161.47	
(Aromatic	carbons),	162.02	(‐CH=N‐).	MS/ESI	(m/z):	Calcd:	310	
[M+],	Found	311	[M+1],	312	[M+2].	

N‐(4‐(Octyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methanamine	
(2e):	 Yield:	 85%	 (C21H28N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2950	 (C‐H	
aliphatic),	 1625	 (C=N),	1539	 (C=C),	1040	 (C‐O).	 1H	NMR	 (300	
MHz,	CDCl3,	δ):	0.89	(t,	3H,	J	=	6.7	Hz,	‐CH3),	1.29	(m,	10H,	CH3‐
(CH2)5‐),	1.79	(quint,	2H,	 ‐CH2‐CH2‐O),	3.99	(t,	2H,	 J	=	6.7	Hz,	 ‐
CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.92	(d,	2H,	J	=	9.0	Hz,	Ar‐H),	
7.29	(d,	1H,	J	=	6.7	Hz,		Ar‐H),		7.70	(d,	1H,	J	=	7.9	Hz,	Ar‐H),	7.71	
(d,	2H,	J	=	9.0	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	8.51	(dd,	1H,		J	=	4.5	
Hz,	 Ar‐H),	 8.60	 (s,	 1H,	 ‐CH=N).	 13C	 NMR	 (75	 MHz,	 CDCl3,	 δ,	
ppm):	 13.96,	 22.48,	 25.86,	 28.88,	 29.00,	 29.17,	 31.65	
(Methylene	 carbons),	 62.08	 (‐CH2‐N),	 67.98	 (‐O‐CH2‐CH2‐),	
114.41,	123.26,	128.38,	129.72,	131.81,	135.04,	135.42,	148.13,	
149.18,	 161.40	 (Aromatic	 carbons),	 162.01	 (‐CH=N‐).	 MS/ESI	
(m/z):	Calcd:	324	[M+],	Found	347	[M+Na].	

N‐(4‐(Decyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methanamine	
(2f):	 Yield:	 82%	 (C23H32N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2895	 (C‐H	
aliphatic),	 1620	 (C=N),	1539	 (C=C),	1020	 (C‐O).	 1H	NMR	 (300	
MHz,	CDCl3,	δ,	ppm):	0.88	(t,	3H,	J	=	6.7	Hz,	‐CH3),	1.27	(m,	14H,	
CH3‐(CH2)7‐),	 1.79	 (quint,	 2H,	 ‐CH2‐CH2‐O),	 3.99	 (t,	 2H,	 J	 =	 6.6	
Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.93	(d,	2H,	J	=	8.5	Hz,	Ar‐
H),	7.28	(d,	1H,	J	=	6.7	Hz,		Ar‐H),	7.67	(d,	1H,	J	=	8.0	Hz,	Ar‐H),	
7.71		(d,	2H,	J	=	8.8	Hz,	Ar‐H),	8.35	(s,	1H,	‐CH=N‐),	8.51	(dd,	1H,	
J	=	4.5	Hz,	Ar‐H),		8.60	(s,	1H,	‐CH=N).	13C	NMR	(75	MHz,	CDCl3,	
δ,	ppm):	13.99,	22.54,	25.85,	28.91,	29.03,	29.16,	29.43,	31.76	
(Methylene	 carbons),	 62.11	 (‐CH2‐N),	 68.01	 (‐O‐CH2‐CH2‐),	
114.44,	123.32,	129.75,	132.22,	135.33,	139.87,	149.18,	161.07	
(Aromatic	carbons),	162.07	(‐CH=N‐).	MS/ESI	(m/z):	Calcd:	352	
[M+],	Found	353	[M+1],	354	[M+2].	

N‐(4‐(Dodecyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methan	
amine	(2g):	Yield:	85%	(C25H36N2O).	FT‐IR	(νmax,	cm‐1):	2891	(C‐
H	aliphatic),	1610	(C=N),	1529	(C=C),	1039	(C‐O).	1H	NMR	(300	
MHz,	CDCl3,	δ,	ppm	):	0.89	(t,	3H,	J	=	6.7	Hz,	‐CH3),	1.27	(m,	18H,	



262	 Yarra	et	al.	/	European	Journal	of	Chemistry	5	(2)	(2014)	260‐262	
	
CH3‐(CH2)9‐),	1.79	(quint,	2H,	‐CH2‐CH2‐O),	3.99(t,	2H,	J	=	6.6	Hz,	
‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.92	(d,	2H,	J	=	9.0	Hz,	Ar‐H),	
7.28	(d,	1H,	J	=	6.8	Hz,	Ar‐H),	7.67	(d,	1H,	J	=	8.0	Hz,	Ar‐H),	7.71	
(d,	2H,	J	=	8.9	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	8.51	(dd,	1H,	J	=	4.0	
Hz,	 	 Ar‐H),	 8.60	 (s,	 1H,	 ‐CH=N).	 13C	 NMR	 (75	 MHz,	 CDCl3,	 δ,	
ppm):	 14.01,	 21.54,	 22.34,	 24.82,	 25.85,	 28.91,	 29.03,	 29.43,	
30.24,	31.56,	32.85	(Methylene	carbons),	61.15	(‐CH2‐N),	69.10	
(‐O‐CH2‐CH2‐),	114.54,	122.39,	129.67,	132.32,	134.50,	138.57,	
148.14,	 149.19,	 161.12	 (Aromatic	 carbons),	 162.04	 (‐CH=N‐).	
MS/ESI	(m/z):	Calcd:	380	[M+],	Found	381	[M+1],	382	[M+2].	

N‐(4‐(Tetradecyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methan	
amine	 (2h):	 Yield:	 68%	 (C27H40N2O).	 FT‐IR	 (νmax,	 cm‐1):	 2895	
(C‐H	 aliphatic),	 1620	 (C=N),	 1520	 (C=C),	 1039	 (C‐O).	 1H	NMR	
(300	MHz,	CDCl3,	δ,	ppm):	0.89	(t,	3H,	J	=	6.7	Hz,	‐CH3),	1.26	(m,	
22H,	CH3‐(CH2)11‐),	1.78	(quint,	2H,	‐CH2‐CH2‐O),	3.99	(t,	2H,	J	=	
6.6	Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.92	(d,	2H,	J	=	8.6	Hz,	
Ar‐H),	7.28	(d,	1H,	J	=	6.9	Hz,	Ar‐H),	7.68	(d,	1H,	J	=	8.0	Hz,	Ar‐
H),	7.71(d,	2H,	J	=	8.0	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	8.50	(dd,	1H,	
J	=	4.5	Hz,		Ar‐H),	8.61	(s,	1H,	‐CH=N).	13C	NMR	(75	MHz,	CDCl3,	
δ,	ppm):	14.01,	21.54,	22.34,	24.82,	25.85,	28.91,	29.16,	29.43,	
30.24,	30.56,	31.08,	31.56,	32.85	(Methylene	carbons),	61.05	(‐
CH2‐N),	 69.14	 (‐O‐CH2‐CH2‐),	 114.50,	 122.40,	 129.70,	 132.66,	
135.23,	 138.61,	 148.04,	 149.22,	 161.02	 (Aromatic	 carbons),	
162.14	 (‐CH=N‐).	 MS/ESI	 (m/z):	 Calcd:	 408	 [M+],	 Found	 409	
[M+1].	

N‐(4‐(Hexadecyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methan	
amine	 (2i):	 Yield:	 80%	 (C29H44N2O).	 FT‐IR	 (νmax,	 cm‐1,	 KBr):	
2890	 (C‐H	aliphatic),	 1621	 (C=N),	1540	 (C=C),	1040	 (C‐O).	 1H	
NMR	 (300	MHz,	 CDCl3,	 δ,	 ppm):	 0.88	 (t,	 3H,	 J	 =	 6.7	Hz,	 ‐CH3),	
1.27	(m,	26H,	CH3‐(CH2)13‐),	1.78	(quint,	2H,	‐CH2‐CH2‐O),	3.98	
(t,	2H,	J	=	6.6	Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.92	(d,	2H,	
J	=	8.6	Hz,	Ar‐H),	7.29	(d,	1H,	J	=	6.5	Hz,		Ar‐H),	7.69	(d,	1H,		J	=	
8.6	Hz,	Ar‐H),	7.71	(d,	2H,		J	=	8.6	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	
8.51	(dd,	1H,	 J	=	4.5	Hz,	 	Ar‐H),	8.60	(s,	1H,	 ‐CH=N‐).	 13C	NMR	
(75	 MHz,	 CDCl3,	 δ,	 ppm):	 14.06,	 22.54,	 25.85,	 29.42,	 29.63	
(Methylene	carbons),	31.86	for	methylene	carbon,	62.17	(‐CH2‐
N),	 68.09	 (‐O‐CH2‐CH2‐),	 114.52,	 123.36,	 129.82,	 131.99,	
135.14,	 134.64,	 148.11,	 149.23,	 161.50	 (Aromatic	 carbons),	
162.12	 (‐CH=N‐).	 MS/ESI	 (m/z):	 Calcd:	 436	 [M+],	 Found	 437	
[M+1],	438	[M+2].	

N‐(4‐(Octadecyloxy)benzylidene)‐1‐(pyridin‐3‐yl)methan	
amine	 	 (2j):	 Yield:	 81%	 (C31H48N2O).	 FT‐IR	 (νmax,	 cm‐1,	 KBr):	
2890	 (C‐H	aliphatic),	 1620	 (C=N),	1540	 (C=C),	1040	 (C‐O).	 1H	
NMR	 (300	MHz,	 CDCl3,	 δ,	 ppm):	 0.87	 (t,	 3H,	 J	=	6.7	Hz,	 ‐CH3),	
1.26	(m,	30	H,	CH3‐(CH2)15‐),	1.78	(quint,	2H,	‐CH2‐CH2‐O),	3.99	
(t,	2H,	J	=	6.7	Hz,	‐CH2‐O),	4.78	(s,	2H,	‐CH2‐N=CH‐),	6.93(d,	2H,	J	
=	9.0	Hz,	Ar‐H),	7.28	(d,	1H,	 	J	=	6.5	Hz,	Ar‐H),	7.67	(d,	1H,	 	J	=	
9.0	Hz,	Ar‐H),	7.70	(d,	2H,	J	=	9.0	Hz,	Ar‐H),	8.35	(s,	1H,	Ar‐H),	
8.51	(dd,	1H,	J	=	4.5	Hz,	Ar‐H),	8.60	(s,	1H,	‐CH=N‐).	13C	NMR	(75	
MHz,	CDCl3,	δ,	ppm):	14.05,	22.63,	25.92,	29.09,	29.61	(Identical	
methylene	carbons),	31.73	(Methylene	carbon),	62.16	(‐CH2‐N),	
68.04	 (‐O‐CH2‐CH2),	 114.47,	 123.34,	 128.44,	 129.77,	 131.50,	
132.6,	 135.50,	 148.22,	 149.24,	 161.45	 (Aromatic	 carbons),	
162.07	 (‐CH=N‐).	 MS/ESI	 (m/z):	 Calcd:	 464	 [M+],	 Found	 465	
[M+1],	466	[M+2].	
	
3.	Results	and	discussion		
	

Etherification	was	carried	out	by	the	reaction	of	Schiff	base	
with	 fatty	 alkyl	 bromides	 of	 different	 chain	 lengths	 in	 the	
presence	of	base	like	potassium	carbonate.	Different	fatty	alkyl	
bromides	 employed	 were	 butyl	 (C4),	 pentyl	 (C5),	 hexyl	 (C6),	
heptyl	 (C7),	 octyl	 (C8),	 decyl	 (C10),	 dodecyl	 (C12),	 tetradecyl	
(C14),	 hexadecyl	 (C16),	 octadecyl	 (C18)	bromides.	The	 structure	
of	the	Schiff	base	ethers	was	confirmed	by	FT‐IR,	 1H	NMR,	13C	
NMR	and	Mass	Spectral	Studies.	These	synthesized	compounds	
will	 be	 evaluated	 for	 biological	 properties	 as	 an	 extension	 to	
the	presence	of	work	and	the	influence	of	different	alkyl	chain	
lengths	 on	 the	 activity	 will	 be	 studied.	 The	 synthesis	 of	
different	Schiff	base	ethers	was	carried	out	using	the	following	
procedure.	

Schiff	 base	 was	 prepared	 by	 a	 mixture	 of	 equimolar	
quantities	 of	 4‐hydroxy	 benzaldehyde	 with	 3‐aminomethyl	
pyridine	 in	 absolute	 ethanol	 under	 reflux	 to	 give	 the	
corresponding	 Schiff	 base	 [16].	 The	 1H	 NMR	 spectra	 of	 Schiff	
base	 showed	 a	 signal	 at	 8.5‐8.6	 ppm	 which	 confirmed	 the	
proton	 indicating	 the	 presence	 of	 azomethine	 group	 (‐CH=N).	
The	 Schiff	 base	 (1)	 was	 etherified	 with	 different	 fatty	 alkyl	
bromides	to	give	the	corresponding	Schiff	base	ethers	2a‐j	that	
was	 indicated	by	the	presence	of	a	 triplet	at	3.96‐4.01	ppm	in	
1H	NMR	spectra.	The	synthesised	Schiff	base	ethers	were	also	
characterized	 by	 FT‐IR	 which	 showed	 the	 presence	 of	 C‐O	
stretching	 frequency	 at	 1039	 cm‐1.	 Mass	 spectra	 of	 the	
synthesized	Schiff	base	ethers	showed	characteristic	molecular	
ions	as	indicated	by	their	molecular	formulae.	
	
4.	Conclusion	
	

In	the	present	study,	we	have	focused	on	the	synthesis	and	
characterization	of	a	series	of	10	new	(4‐alkyloxybenzylidene)‐
pyridin‐3‐ylmethylamine‐Schiff	 base	 ethers	 (2a‐j)	 for	 the	 first	
time	by	employing	a	two	step	synthetic	route.		The	synthesized	
molecules	were	thoroughly	characterized	using	FT‐IR,	1H	NMR,	
13C	NMR	and	mass	spectral	studies.	These	 	molecules	can	find	
potential	applications	as	anti‐microbial	and	chemotheraupeutic	
agents.		
	
Acknowledgements	
	

The	 author	 Mohini	 Yarra	 is	 thankful	 to	 the	 Council	 for	
Scientific	 Industrial	 Research‐Indian	 Institute	 of	 Chemical	
Technology	for	providing	the	grants	to	carry	out	this	work.	
	
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