Acetone → 5-Chloro-N-[1-(2-chlorophenyl)-2-(1-isopropylpiperidin-4-yl-methoxy)ethyl]-1H-indole-2-carboxamide

HRID 32430Notes

Reaction equation

HRID 32430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[CH2:15][O:16][CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:12])=[CH:5]2.[CH3:31][C:32]([CH3:34])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[CH2:15][O:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([CH:32]([CH3:34])[CH3:31])[CH2:22][CH2:23]1)=[O:12])=[CH:5]2

Participants

3

Reactant 2

HCID 180AcetoneHCID 693096485-chloro-N-[1-(2-chloro-phenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-2-carboxamide

Product 1

HCID 693130255-Chloro-N-[1-(2-chlorophenyl)-2-(1-isopropylpiperidin-4-yl-methoxy)ethyl]-1H-indole-2-carboxamide

Procedure

Using alkylation method A, 5-chloro-N-[1-(2-chloro-phenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-2-carboxamide (320 mg, 0.72 mmol) and acetone (2.0 mL, 27 mmol) afforded, after purification (SiO2: 0 to 2.5% isopropylamine in 1:1 hexane:EtOAc) and recrystallization (acetonitrile), 185 mg (53%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 0 to 2.5% isopropylamine in 1:1 hexane:EtOAc) and recrystallization (acetonitrile), 185 mg (53%) of the title compound

Sources & evidence

ORD record
ord-856810d339f04c569bb43603a677e55d
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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