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

HRID 32451Notes

Reaction equation

HRID 32451 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:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:16][O:17][CH2:18][CH2:19][CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1.[CH2:32]=O>>[ClH:2].[Cl:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][C@H:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:16][O:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([CH3:32])[CH2:24][CH2:25]3)=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 69309604HCID 69309604, compound

Product 1

HCID 693131843-Chloro-N-[(R)-1-phenyl-2-[2-(1-methylpiperidin-4-yl)-ethoxy]ethyl]-1H-indole-6-carboxamide hydrochlorideYield 137.6%

Procedure

Using alkylation method B, 3-chloro-N-[(R)-1-phenyl-2-[2-(piperidin-4-yl)ethoxy]ethyl]-1H-indole-6-carboxamide hydrochloride (300 mg, 0.65 mmol) and paraformaldehyde (195 mg, 6.5 mmol) afforded 213 mg (75%) of the title compound.

Sources & evidence

ORD record
ord-50fd19aeef6c4b42a91184c0a3782547
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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