Formaldehyde → 3-Chloro-N-[(R)-1-phenyl-2-(1-methylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide

HRID 32419Notes

Reaction equation

HRID 32419 reaction equation
Cl.[Cl:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][C@H:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:16][O:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1.[CH2:31]=O>>[Cl:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][C@H:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:16][O:17][CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([CH3:31])[CH2:23][CH2:24]3)=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 69307898HCID 69307898, compound

Product 1

HCID 693106013-Chloro-N-[(R)-1-phenyl-2-(1-methylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide

Procedure

Using alkylation method B, 3-chloro-N-[(R)-1-phenyl-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide hydrochloride (200 mg, 0.44 mmol) and paraformaldehyde (134 mg, 4.4 mmol) afforded, after purification (SiO2: 2.5% isopropylamine in 10:2:2:DCM:EtOAc:hexane), 80 mg (42%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 2.5% isopropylamine in 10:2:2:DCM:EtOAc:hexane), 80 mg (42%) of the title compound

Sources & evidence

ORD record
ord-0b42e336fc9d428ea407c9443f8ab370
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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