1H-Indole-3-carboxylic acid, 2-chloro- → N-[(1-n butyl-4-piperidyl)methyl]2-chloroindole-3-carboxamide

HRID 1458614

Reaction equation

HRID 1458614 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([OH:13])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:14]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1)[CH2:15][CH2:16][CH3:17].C(N1CCC(CNC(C2C3C(=CC=CC=3)NC=2)=O)CC1)CCC>>[CH2:14]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[Cl:1])=[O:13])[CH2:20][CH2:19]1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 995211H-Indole-3-carboxylic acid, 2-chloro-HCID 104421334-Aminomethyl-1-N-butylpiperidineHCID 10591304N-[(1-n butyl-4-piperidyl)methyl] indole-3-carboxamide

Product 1

HCID 22096969N-[(1-n butyl-4-piperidyl)methyl]2-chloroindole-3-carboxamide

Procedure

2-Chloroindole-3-carboxylic acid (L. Marchetti and A Andreani, Ann. Chim. (Rome), 1973, 63, 681) was converted to its acid chloride and reacted with N-(1-n butyl-4-piperidyl)methylamine (D 1) using the procedure of Description 1b to afford N-[(1-n butyl-4-piperidyl)methyl] 2-chloroindole-3-carboxamide.

Sources & evidence

ORD record
ord-f9cda446b9ad40d18ad12f05a1e650df
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Linked notes

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