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

HRID 1463112Notes

Reaction equation

HRID 1463112 reaction equation
Cl[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>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

5

Reactant 2

HCID 260Hydrogen BromideHCID 28175763-(2-Chloro-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 6212ChloroformSolvent2×

Procedure

Using chloroform as solvent. A solution of 3-(2-chloro-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one (5.12 g) in chloroform (50 ml) was treated with 48% HBr in acetic acid (2 ml). After 12 hours the organic solvent was removed under reduced pressure and the residue triturated with aqueous ammonia to yield the title compound m.p. 192°-3° C. (EtOAc).

Workup

  1. customAfter 12 hours the organic solvent was removed under reduced pressure
  2. customthe residue triturated with aqueous ammonia

Sources & evidence

ORD record
ord-dfbbad517cf14e5ca5b7f1b94c99ad8b
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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