4-(4-Chlorophenethyl)piperazin-2-one → tert-Butyl 7-(4-(4-chlorophenethyl)-2-oxopiperazin-1-yl)-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 2365422Notes

Reaction equation

HRID 2365422 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([CH3:23])[CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]2)=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][N:34]([C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([CH3:23])[CH2:12][C:7]=5[N:8]([CH3:11])[C:9]=4[CH:10]=3)[C:33](=[O:37])[CH2:32]2)=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 580922294-(4-Chlorophenethyl)piperazin-2-oneHCID 67986822tert-Butyl 7-bromo-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 67986825tert-Butyl 7-(4-(4-chlorophenethyl)-2-oxopiperazin-1-yl)-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 34%

Procedure

tert-Butyl 7-bromo-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (enantiomer A) (1.00 g, 2.64 mmol) and 4-(4-chlorophenethyl)piperazin-2-one (0.754 g, 3.16 mmol) were reacted following the procedure for Example 2 (step f) to provide the title compound (482 mg, 34%) as a foam: ESI MS m/z 538 [M+H]+.

Sources & evidence

ORD record
ord-629c485765ef4619a5e5f6c9959a12b5
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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