2-Chloro-3,4-dimethoxyphenethylamine → 6-chloro-7,8-dihydroxy-1-(m-trifluoromethylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide
Reaction equation
[Cl:1][C:2]1[C:10]([O:11]C)=[C:9]([O:13]C)[CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].[F:15][C:16]([F:29])([F:28])[C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[CH2:20][CH:21]([Br:24])OC>>[BrH:24].[Cl:1][C:2]1[C:3]2[CH2:4][CH2:5][NH:6][CH2:21][CH:20]([C:19]3[CH:25]=[CH:26][CH:27]=[C:17]([C:16]([F:15])([F:28])[F:29])[CH:18]=3)[C:7]=2[CH:8]=[C:9]([OH:13])[C:10]=1[OH:11]Participants
3
Procedure
A mixture of 8.0 g of 2-chloro-3,4-dimethoxy-phenethylamine and 5.25 g of m-trifluoromethyl-α-methoxy-phenethylbromide is heated at 100°-105° for 21/2 hours. The product was partitioned between ethyl acetate and 5% sodium bicarbonate solution. The organic layer was removed, washed with brine, dried and concentrated. The residue was passed over 350 g of silica gel with 1 to 2% methanol/chloroform. The resulting product was an oil whose hydrochloride melted at 200°-202°. The oily base (2.5 g) was heated with 50 ml of 48% hydrogen bromide and worked up as above to give the desired 6-chloro-7,8-dihydroxy-1-(m-trifluoromethylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. ~250°.
Workup
- temperatureis heated at 100°-105° for 21/2 hours
- customThe product was partitioned between ethyl acetate and 5% sodium bicarbonate solution
- customThe organic layer was removed
- washwashed with brine
- customdried
- concentrationconcentrated
- temperatureThe oily base (2.5 g) was heated with 50 ml of 48% hydrogen bromide
Sources & evidence
- ORD record
- ord-1521089e4760427f8f7caacfb1eb6703
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04359464
Reaction notes
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