J. Chem. Sci. (2 0 2 0 ) 13 2: 92
P age 5 of 7 92
to th e r ea c ti on m ixt ur e. The r ea c ti on wa s st ir r e d a t
r oom te m pe ra t ur e. The in or ga nic sa lt wa s r em o ve d by
fi ltr a ti on a nd r ins ed twi ce wit h di ch lor om e tha n e. The
sol uti on wa s po ur ed in to wa te r a nd e xtr a c te d w ith
di ch lor om e tha ne ( 2 x 25 m l) . The c om bine d or ga nic
la ye r s we r e wa she d wit h br in e, dr ie d ov er a nh ydr ous
sod ium sul pha te , fi lte r e d, a nd c onc e ntr a te d in va c uo
r es ult ing in th e f or ma t ion of th e pr od uct in 92 % yie ld
wit h c oupl ing r at io 1: 1 a nd pr od uct yi el d 78 % w ith
c oupl ing r at io 2: 1. N- a lkyl at ion of he te r oc yc le s w ith
1,3 -d ibr om opr op ane ha vi ng 1: 1 c oupl ing pr o por tion
(
(
Sc he m e- 2 ) is e as ie r th an 2: 1 c oupl ing pr o por tion
Sc he m e- 3 ).
Figure 1. X- ra y
[
po w d er
di f fr a ct og ra m
com pl ex
1-(3-bromopropyl)-1H-indole (1c)
Yie ld 92% [ C H NB r]
Cu (L ) (p h e n )C l 2 ].
1
1 1 2
1
H NMR ( CDC l , 300 MHz ) d 7.7 0–6. 56( Ar- H) , d
3
Adsorption / desorption isotherm
1 3
2
1
1
.8 0 ( 2H, t) , d 2.8 5 ( 2H, m ), d 2.9 0 ( 2H, t) . C N MR :
63 .2, 136 .3, 128 .7, 12 5.3, 12 4.5, 12 3.1, 12 0.2, 110.4 ,
04 .4, 38 .8, 32. 7 ppm .
1
8
2
6
0
MS ( ES ): m/z= 238 [ M] ?.
1, 1-(propane-1, 3-diyl) di(1H-indole) (2c)
Yie ld 75% [ C H N ]
1
1
9 1 8 2
1
H NMR ( CDC l , 300 MHz ) d 7.6 6–6.8 5 ( Ar - H) , d
3
2
.6 2 ( 2H, t) , d 2.7 8 ( 2H, m ), d 2.8 3 ( 2H, t) .
1 3
C NMR : 186 .3, 17 6.8, 169 .4, 16 6.5, 163 .4 , 159.7 ,
56 .2, 136 .8, 131 .1, 12 3.3, 12 2.5, 12 1.1, 12 0.5, 109.4 ,
1
0
0.5
1
107 .9, 10 0.9, 99. 5, 40 .4, 36 .8 pp m.
p/p0
MS ( ES ): m/z= 273 [ M] ?.
ADS
DES
Figure 2. B ET cu rv e of co m pl e x [ N i( L) (P P h ) C l ].
3
2
2
4. Probable mechanism of N-alkylation of indole
with 1,3-dibromopropane
3
. Experimental Section
. 1 Synthesis of Schiff base and their transition
metal complexes
The po ssib le m ec ha ni sm f or th e N- a lkyl at ion of indo le
wit h 1,3 -d ibr om opr op ane is il lus tr at ed . I nit ia lly 1,3-
di br om opr opa ne is ox ida tiv el y a dde d to Nic ke l ( I I )
c om ple x i.e . c om poun d ( I ) to gi ve c om poun d ( I I ) . The
se c onda r y he te r oc yc le in dole c oor di na te to N ic ke l
c en te r to f or m c om poun d ( I II ) a nd c om poun d ( I II ) a ga in
a ct iva te in pr e se nc e of ba se wit h r em ov al of hydr og en
br om ide . F ina ll y c hlo ri ne io ns f r om out e r s phe r e
tr a nsf e r re d to in ne r sph er e wit h f or ma t ion of N -A lky-
la te d pr od uct ( N- (3 -b ro mopr o pyl) in dole ) a nd ge ne r a te
th e c or r esp ondi ng c om ple x c at al yst ( Fi gur e 3 ) .
3
Th e S c h iff b a s e 2 - Phe ny l , 3- b enz yl a mi no , 1, 2- di hy-
d ro q u in a z o l i -4 (3 H )- on e ( PBADQ) i s sy nt h es i ze d by
m o di fi e d re p o rte d me th od . Sc hi f f ba se and th ei r
t ra ns i ti o n me t a l Co (I I) , Ni (I I ), Cu (I I) an d Zn( I I )
c o mp le x e s C- 1 to C- 12 wer e sy nt h es iz ed by m odifi e d
18
19 – 21
re p o rte d me t h o d .
3 . 2 General procedure for N-alkylation
of heterocycles with 1,3-dibromopropane
5. Conclusion
Th e g e n e ra l p ro c e du re f or t he N- al ky la t io n o f he te r o-
2
2
The c at al yti c r ole of c om ple xe s 1– 12 we r e te s te d f or
N- a lkyl at ion of di ff e r en t he te r oc yc le s wit h 1,3 - dibr o-
m opr opa ne . I t wa s obs er ve d th at a ll th e c ompl ex es
wor ke d a s th e e ffi c ie nt c at al yst s. Esp e c ia lly
c y c le s wa s a s fo ll o ws. Het e ro cy cl e ( 1 mm ol) wa s
d i s so l v e d in 5 ml an hy dr ou s DM F. Th en c om ple x
(
0 . 0 5 mm o l) a n d K CO was ad de d t o t he so l uti on a t
2 3
ro o m te m p e ra tu re . Sh or t ly af t er war ds ( 20 m in) ,
, 3 - d ib ro mo p r o p a ne ( 1 mmo l ) was ad de d i n po rt ion s
[
Ni( L) ( PP h ) C l ] c om ple x is m or e sui ta bl e f or the s e
3 2 2
1