Acetaldehyde → 3-Chloro-N-[1-(2-chlorophenyl)-2-(1-ethylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide

HRID 32425

Reaction equation

HRID 32425 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH:31](=O)[CH3:32]>>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:31][CH3:32])[CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 693078883-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

Product 1

HCID 444440863-Chloro-N-[1-(2-chlorophenyl)-2-(1-ethylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide

Procedure

Using alkylation method A, 3-chloro-N-[1-(2-chloro-phenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (600 mg, 1.3 mmol) and acetaldehyde (0.4 mL, 6.7 mmol) afforded, after purification (SiO2: 10:10:1 hexane:EtOAc:isopropylamine) and recrystallization (acetonitrile), 275 mg (43%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 10:10:1 hexane:EtOAc:isopropylamine) and recrystallization (acetonitrile), 275 mg (43%) of the title compound

Sources & evidence

ORD record
ord-17395d43aa494cd5984f29920228c68a
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Linked notes

Loading…