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

HRID 972338Notes

Reaction equation

HRID 972338 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 two 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 two 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-95ab69296c9c4d088c957acf22c4cd3c
Source dataset
uspto-grants-1977_10
Patent number
US04052506

Reaction notes

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