Methanol → 3-Ethyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 972349Notes

Reaction equation

HRID 972349 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH2:22](Br)[CH3:23].[OH-].[K+].CO>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][N:9]([CH2:22][CH3:23])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 105409631H-3-Benzazepine, 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-

Product 1

HCID 214066873-Ethyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A sample of 7,8-dimethoxy-1-phenyl-2,3,4,5,-tetrahydro-1H-3-benzazepine weighing 4.32 g. (0.0154 mol), 2.18 g. (0.02 mol) of ethyl bromide and 1.12 g. (0.02 mol) of potassium hydroxide are dissolved in 120 ml. of dry methanol and the solution is refluxed overnight. Evaporation of the solution to dryness gives a mixture which is taken up in ethyl acetate and filtered to remove inorgaic salts. The filtrate is washed with water, dried and evaporated to give 7,8-dimethoxy-3-ethyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine as an oil.

Workup

  1. customEvaporation of the solution to dryness
  2. customgives a mixture which
  3. filtrationfiltered
  4. customto remove inorgaic salts
  5. washThe filtrate is washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-0eef670453494b7bb628cf3fcf679a1e
Source dataset
uspto-grants-1977_10
Patent number
US04052506

Reaction notes

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