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

HRID 2365414Notes

Reaction equation

HRID 2365414 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.[F: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>>[F: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 575147614-(4-Fluorophenethyl)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 67986823tert-Butyl 7-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 58%

Procedure

tert-Butyl 7-bromo-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (enantiomer A) (180 mg, 0.474 mmol) and 4-(4-fluorophenethyl)piperazin-2-one (104 mg, 0.474 mmol) were reacted following the procedure for Example 2 (step f) to provide the title compound (144 mg, 58%) as a yellow solid: ESI MS m/z 521 [M+H]+.

Sources & evidence

ORD record
ord-7f06e2fbf3fd4aee832ccfaf4cf76047
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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