Download (4Mb) - Etheses - Saurashtra University

Part-A Studies on 2-methyl indoline derivatives…..
Furthermore, literature 107-118 revealed many synthetic procedures to
synthesize 2-methyl indoline and its derivatives through cyclization and
reduction.
A.2.3 N-ALKYLATION ON 2-METHYL INDOLINE
Indolines (1) (n = 1, 2, R = H, Me; NR 1 R 2 = piperidino, morpholino, 2methylpiperidino-1-indolinyl,
tetrahydro-2-isoquinolyl; R 1 = R 2 = ethyl, propyl,
isopropyl, etc.) were prepared by Sheinkman et. al. 119 in 18-96% yield by
reaction of (2) with HNR 1 R 2 . (2) were prepared by reaction of Cl(CH2)nCOCl
with the respective indoline. (3) was obtained by reaction of 1-(2-chloroethyl)
piperidine and indole and also by reduction of (1) (R = H, n = 1, NR 1 R 2 =
piperidino) using LiAlH4. (1) had weak anesthetic activity; (1) (R = H, n = 1, R 1
= R 2 = isopropyl) was the most active anesthetic; (1) (NR 1 R 2 = piperidino, R =
H, Me, n = 1, 2) were the most effective local anesthetics. (Fig. A.5)
Fig. A.5
The title compounds (1) (R = diethylamino, morpholino; R 1 = R 3 = H;
R 1 R 3 = bond; R 2 = R 5 = H, methyl; R 4 = H, methyl, ethyl), (2), and (3) (R 6 = H,
methyl; R 7 = diethylamino, morpholino) were prepared by Mutschler et. al. 120
by the reaction of diethylamine or morpholine with the corresponding
chloroacetylindoles or chloroacetylindolines, which were prepared by the
reaction of the parent compounds with chloroacetylchloride. (Fig. A.6)
Department of Chemistry, Saurashtra University, Rajkot – 360 005 19