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

HRID 1463114Notes

Reaction equation

HRID 1463114 reaction equation
Br[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>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

5

Reactant 2

HCID 260Hydrogen BromideHCID 131888373-(2-Bromo-3-oxocyclohex-1-enyl)-3-ethylhexahydro-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-bromo-3-oxocyclohex-1-enyl)-3-ethylhexahydro-1-methylazepin-2-one (6.57 g) in dichloromethane (70 ml) was treated with 48% HBr in acetic acid (1 ml). After 3 hours NMR indicated completion. The solvent was removed under reduced pressure and the residue triturated with aqueous ammonia to yield the title compound as a white crystalline solid, m.p. 178°-80° C. (EtOAc).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue triturated with aqueous ammonia

Sources & evidence

ORD record
ord-c8d6ffe6109d4ece84355f2a3210b958
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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