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

HRID 1463111Notes

Reaction equation

HRID 1463111 reaction equation
Br[C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17].Br.N>C(Cl)(Cl)Cl.C(O)(=O)C>[OH:8][C:7]1[CH:2]=[C:3]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]2=[O:17])[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 131888363-(2-Bromo-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one

Product 1

HCID 11746121hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-bromo-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one (6 g) in chloroform (60 ml) was treated with 48% HBr in acetic acid (1 ml). After 4 hours, NMR indicated completion. Aqueous ammonia was added and the organic solvent removed under reduced pressure to yeild the title compound as a crystalline solid, m.p. 192°-3° (EtOAc).

Workup

  1. customthe organic solvent removed under reduced pressure

Sources & evidence

ORD record
ord-79187fe953d7489994ae276f6fccbd01
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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