Styrene Oxide → HCID 70606246, compound

HRID 426743Notes

Reaction equation

HRID 426743 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][NH2:14])[CH:6]=[C:7]([CH3:11])[C:8]=1[O:9][CH3:10].[CH2:15]1[O:23][CH:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[OH:23][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12][C:5]1[CH:6]=[C:7]([CH3:11])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 13697587HCID 13697587, compound

Product 1

HCID 70606246HCID 70606246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Phenyl-7,8-dihydroxy-9-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine is obtained by treating 2-(3,4-dimethoxy-5-methylphenyl)ethylamine in tetrahydrofuran with styrene oxide for 12 hours as described above to give N-[(2-hydroxy-2-phenylethyl)]-2-(3',4'-dimethoxy-5-methylphenyl)ethylamine which on cyclization gives the 7,8-dimethoxy benzazepine. Cleavage of this as described gives the desired 6-methyl compound as the hydrobromide which may be converted via the free base to the hydrochloride.

Sources & evidence

ORD record
ord-efa8ac69fcfa431b9c47a99426e9e247
Source dataset
uspto-grants-1979_10
Patent number
US04171359

Reaction notes

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