2-Chloro-3,4-dimethoxyphenethylamine → 6-chloro-7,8-dihydroxy-1-(m-trifluoromethylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

HRID 971613노트

반응식

HRID 971613 반응식
[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]

참가 물질

3

반응물 2

HCID 30177522-Chloro-3,4-dimethoxyphenethylamineHCID 20518146m-Trifluoromethyl-alpha-methoxyphenethylbromide

생성물 1

HCID 129097936-chloro-7,8-dihydroxy-1-(m-trifluoromethylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

실험 절차

A mixture of 8.0 g of 2-chloro-3,4-dimethoxy-phenethylamine and 5.25 g of m-trifluoromethyl-α-methoxyphenethylbromide is heated at 100°-105° for 21/2 hours. The product was partitioned betwen 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°.

후처리

  1. temperatureis heated at 100°-105° for 21/2 hours
  2. customThe product was partitioned betwen ethyl acetate and 5% sodium bicarbonate solution
  3. customThe organic layer was removed
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. temperatureThe oily base (2.5 g.) was heated with 50 ml of 48% hydrogen bromide

출처 및 근거

ORD 기록
ord-ba52e9a605134e649e372a4ce8932182
출처 데이터셋
uspto-grants-1979_07
특허 번호
US04160765

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