1-Phenylpiperazine → 2-(4-Phenyl-piperazin-1-yl)-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-one

HRID 1817834Notes

Reaction equation

HRID 1817834 reaction equation
Cl[CH:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH:7]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:6]3[CH2:5][C:4]=2[NH:3]1.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.CCOC(C)=O>[C:17]1([N:23]2[CH2:28][CH2:27][N:26]([C:2]3[CH:11]=[CH:10][C:9]4[C:8](=[O:12])[CH:7]5[CH2:13][CH2:14][CH2:15][CH2:16][CH:6]5[CH2:5][C:4]=4[N:3]=3)[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 690381592-chloro-2,5a,6,7,8,9,9a,10-octahydro-1H-benzo[g]quinolin-5-one

Product 1

HCID 578832202-(4-Phenyl-piperazin-1-yl)-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-oneYield 247.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-chloro-2,5a,6,7,8,9,9a,10-octahydro-1H-benzo[g]quinolin-5-one (0.29 g, 0.123 mmol) and 1-phenylpiperazine (2.0 g, 12.3 mmol) was stirred at 100° C. for 1 h (TLC control; hexane-EtOAc, 2:1). Then the mixture was separated by column chromatography on silica gel to give the title compound (0.11 g, 25%) as a pale yellow solid.

Workup

  1. customThen the mixture was separated by column chromatography on silica gel

Sources & evidence

ORD record
ord-1aa833762e364676989baf168474278f
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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