O-Methyltyramine → HCID 14151504, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[CH2:12]1O[CH:13]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[O:2]([C:3]1[CH:11]=[CH:10][C:6]2[CH2:7][CH2:8][NH:9][CH2:12][CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[CH:4]=1)[CH3:1]Participants
3
Procedure
According to the Procedure A above, 4-methoxyphenethylamine is reacted with styrene oxide and the resulting N-(2-hydroxy-2-phenyl)ethyl-4-methoxyphenethylamine is cyclized with acid to give 8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine. A salt, for example the hydrochloride, of this compound is reacted with bromine to give the 7-bromo compound which is reacted with butyllithium and phenyl disulfide or trifluoromethanesulfenyl chloride to give 8-methoxy-1-phenyl-7-phenylthio(or 7-trifluoromethylthio)-2,3,4,5-tetrahydro-1H-3-benzazepine. The 8-hydroxy compounds are prepared by O-demethylating the 8-methoxy compounds by standard procedures.
Sources & evidence
- ORD record
- ord-504d1d21964c4ae9a536eeb49e0f1093
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04707483
Reaction notes
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