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

HRID 32437Notes

Reaction equation

HRID 32437 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][C:27]([F:30])=[CH:26][CH:25]=3)[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.[CH2:31]=O>>[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][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH3:31])[CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 69309629HCID 69309629, compound

Product 1

HCID 693130873-Chloro-N-[1-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide

Procedure

Using alkylation method B, 3-chloro-N-[1-(4-fluoro-phenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (373 mg, 0.87 mmol) and paraformaldehyde (520 mg, 17 mmol) afforded, after purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine), 115 mg (30%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine), 115 mg (30%) of the title compound

Sources & evidence

ORD record
ord-43c9b695c3ea4d05bc25b760ca2ee2a1
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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