Acetone → N-[1-(2-Chlorophenyl)-2-(1-isopropylpiperidin-4-ylmethoxy)-ethyl]-1H-indole-6-carboxamide

HRID 32432Notes

Reaction equation

HRID 32432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:18][C:19]([C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1)=[O:20])[CH2:9][O:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH3:30][C:31]([CH3:33])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:18][C:19]([C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1)=[O:20])[CH2:9][O:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:31]([CH3:33])[CH3:30])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 180AcetoneHCID 69307887N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

Product 1

HCID 69308011N-[1-(2-Chlorophenyl)-2-(1-isopropylpiperidin-4-ylmethoxy)-ethyl]-1H-indole-6-carboxamide

Procedure

Using alkylation method A, N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (195 mg, 0.47 mmol) and acetone (2.0 mL, 27 mmol) afforded, after purification (SiO2: 0 to 2.5% isopropylamine in 1:1 hexane:EtOAc), 120 mg (60%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 0 to 2.5% isopropylamine in 1:1 hexane:EtOAc), 120 mg (60%) of the title compound

Sources & evidence

ORD record
ord-cf2070b99311469f96ad886db46d166a
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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