Butyl bromide → 3-Butyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2420086Notes

Reaction equation

HRID 2420086 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)[CH2:23][CH2:24][CH3:25].[OH-].[K+]>CO>[CH2:22]([N:9]1[CH2:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:18]=[C:19]([O:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10]1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 105409631H-3-Benzazepine, 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-

Product 1

HCID 203879373-Butyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.32 g. (0.0154 mole) of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, 0.02 mole of n-butyl bromide and 0.02 mole of potassium hydroxide is dissolved in 120 ml. of dry methanol and refluxed for 48 hours. The reaction mixture is evaporated to dryness, taken up in ethyl acetate and filtered to remove inorganic salts. The filtrate is washed with water, dried and evaporated to give 3-n-butyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine as an oil.

Workup

  1. additionA mixture of 4.32 g
  2. customThe reaction mixture is evaporated to dryness
  3. filtrationfiltered
  4. customto remove inorganic salts
  5. washThe filtrate is washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-3b15b2a55c0e49e884dfc8fc19bfff99
Source dataset
uspto-grants-1978_08
Patent number
US04108989

Reaction notes

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