7-chloro-3-(piperidin-4-yl)-1H-indole → 7-Chloro-3-{1-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)butan-1-yl]piperidin-4-yl}-1H-indole, hydrochloride

HRID 2180949Notes

Reaction equation

HRID 2180949 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.Br[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][C:23]1=[O:32]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]1[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][C:23]2=[O:32])[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 120720367-chloro-3-(piperidin-4-yl)-1H-indoleHCID 129923681-(4-Bromobutan-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 1317248717-Chloro-3-{1-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)butan-1-yl]piperidin-4-yl}-1H-indole, hydrochloride

Procedure

from 7-chloro-3-(piperidin-4-yl)-1H-indole and 1-(4-bromobutan-1-yl)-3,4-dihydroquinolin-2(1H)-one. Mp 253-254° C. 1H NMR (DMSO-d6): 1.55-1.65 (m, 2H); 1.75-1.85 (m, 2H); 2.05-2.25 (m, 4H); 2.55 (t, 2H); 2.90 (t, 2H); 2.95-3.15 (m, 5H); 3.55 (d, 2H); 3.95 (t, 2H); 6.95-7.05 (m, 2H); 7.15-7.30 (m, 5H); 7.70 (d, 1H); 10.60 (broad s, 1H); 11.30 (s, 1H). MS m/z: 436 (MH+), 289.

Sources & evidence

ORD record
ord-51fcabde6c1047cb8616f4b15cf4572b
Source dataset
uspto-grants-2005_05
Patent number
US06890916B2

Reaction notes

Loading…