Sulfuric Acid → 1H-3-Benzazepine, 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-

HRID 596610Notes

Reaction equation

HRID 596610 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O.S(=O)(=O)(O)O>>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][NH:13][CH2:12][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 10662045HCID 10662045, compound

Product 1

HCID 105409631H-3-Benzazepine, 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-

Procedure

A solution of 30.1 g. (0.1 mol) of N-[2-(3,4-dimethoxyphenyl)ethyl] -2-phenyl-2-hydroxyethylamine in 120 ml. of trifluoroacetic acid and 8.2 ml. of concentrated sulfuric acid is heated at reflux for 2 hours. After cooling to room temperature, the trifluoroacetic acid is removed under reduced pressure and 100 ml. of ice-water is added. This mixture is basified to pH 9-10 with 10% sodium hydroxide solution and thoroughly extracted with ethyl acetate. The extract is dried and evaporated to give 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine as an oil. Various salts can readily be prepared from the free base. For example, 5 g. (0.0176 mol) dissolved in dry ether is treated with methanesulfonic acid dropwise until no further precipitate is formed. The solid is filtered and washed with dry ether to give 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine methanesulfonate, m.p. 133°-136° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe trifluoroacetic acid is removed under reduced pressure and 100 ml
  3. additionof ice-water is added
  4. extractionthoroughly extracted with ethyl acetate
  5. customThe extract is dried
  6. customevaporated

Sources & evidence

ORD record
ord-9dafa082af6e45378c7a0f8918e3ca70
Source dataset
uspto-grants-1977_03
Patent number
US04011319

Reaction notes

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