Ammonia → 3-Ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

HRID 1463115Notes

Reaction equation

HRID 1463115 reaction equation
Cl[C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=1[C:9]1([CH2:18][CH3:19])[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17].Br.N>ClCCl.C(O)(=O)C>[CH2:18]([C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[CH:2]=2)[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17])[CH3:19]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 131888383-(2-Chloro-3-oxocyclohex-1-enyl)-3-ethyl-hexahydro-1-methylazepin-2-one

Product 1

HCID 27945733-Ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-chloro-3-oxocyclohex-1-enyl)-3-ethyl-hexahydro-1-methylazepin-2-one (5.68 g) in dichloromethane (60 ml) was treated with 48% HBr in acetic acid (2 ml). After 12 hours the mixture was treated with excess aqueous ammonia, the organic solvent removed under reduced pressure and the resulting solid removed by filtration to give the title compound, m.p. 178°-80° C. (EtOAc).

Workup

  1. customthe organic solvent removed under reduced pressure
  2. customthe resulting solid removed by filtration

Sources & evidence

ORD record
ord-ad7d334a45e7495899fda98c50f5296f
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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