N-Methylcyclohexylamine → 2-(Cyclohexyl-methyl-amino)-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-one

HRID 1817833Notes

Reaction equation

HRID 1817833 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.[CH:17]1([NH:23][CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CCCCCC.CCOC(C)=O>[CH:17]1([N:23]([CH3:24])[C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH:7]4[CH2:13][CH2:14][CH2:15][CH2:16][CH:6]4[CH2:5][C:4]=3[N:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 690381592-chloro-2,5a,6,7,8,9,9a,10-octahydro-1H-benzo[g]quinolin-5-one

Product 1

HCID 578831902-(Cyclohexyl-methyl-amino)-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-oneYield 52%

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, 1.23 mmol) and cyclohexyl(methyl)amine (1.39 g, 12.3 mmol) was stirred at 110° C. for 9.5 h (TLC control; hexane-EtOAc, 2:1). Then the mixture was separated by column chromatography on silica gel to give the title compound (0.2 g, 52%) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-eec30a5d33194585ab757ee17a7e16f2
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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