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

HRID 2365408Notes

Reaction equation

HRID 2365408 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])[CH2:13][CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[F:23][C:24]1[CH:38]=[CH:37][C:27]([CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][NH:33][C:32](=[O:36])[CH2:31]2)=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][N:33]([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])[CH2:13][CH2:12][C:7]=5[N:8]([CH3:11])[C:9]=4[CH:10]=3)[C:32](=[O:36])[CH2:31]2)=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 575147614-(4-Fluorophenethyl)piperazin-2-oneHCID 57950375tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 67986820tert-Butyl 7-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 33.5%

Procedure

tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (1.6 g, 4.4 mmol) and 4-(4-fluorophenethyl)piperazin-2-one (0.96 g, 4.3 mmol) were reacted according to Example 2 (step f) to provide the title compound (730 mg, 33%) as a yellow powder: ESI MS m/z 507 [M+H]+.

Sources & evidence

ORD record
ord-585a89aa9a5a4acf9326819bb93641f2
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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