4-(4-Fluorophenethyl)piperazin-2-one → tert-Butyl 8-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-6-methyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate

HRID 474996Notes

Reaction equation

HRID 474996 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][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[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][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 58093439tert-butyl 8-bromo-6-methyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate

Product 1

HCID 58093443tert-Butyl 8-(4-(4-fluorophenethyl)-2-oxopiperazin-1-yl)-6-methyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylateYield 71.6%

Procedure

tert-Butyl 8-bromo-6-methyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate (230 mg, 0.609 mmol) and 4-(4-fluorophenethyl)piperazin-2-one (123 mg, 0.534 mmol) were reacted following the procedure for Example 53 (step b) to provide the title compound (199 mg, 71%) as a colorless oil: ESI MS m/z 521 [M+H]+.

Sources & evidence

ORD record
ord-9e15d30a5ad34aaa93785ceafd204517
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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