Allyl bromide → 3-allyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2286389Notes

Reaction equation

HRID 2286389 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH2:23](Br)[CH:24]=[CH2:25]>C(#N)C>[CH2:25]([N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:13]([O:14][CH3:15])=[CH:12][C:6]=2[CH2:7][CH2:8]1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 129234297,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 234628563-allyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 7 g. (0.0337 mole) of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine dissolved in 170 ml. of acetonitrile and 5 ml. of triethylamine, cooled in an ice bath, was added 4.25 g. (0.035 mole) of allyl bromide in 30 ml. of acetonitrile, dropwise with stirring. The mixture was brought to room temperature and refluxed for 11/2 hours. The reaction mixture was evaporated to dryness, partitioned between ethyl acetate and 5% sodium bicarbonate solution, and the separated ethyl acetate dried and evaporated to give 3-allyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. additionTo a mixture of 7 g
  2. additionwas added 4.25 g
  3. customwas brought to room temperature
  4. temperaturerefluxed for 11/2 hours
  5. customThe reaction mixture was evaporated to dryness
  6. custompartitioned between ethyl acetate and 5% sodium bicarbonate solution
  7. dry with materialthe separated ethyl acetate dried
  8. customevaporated

Sources & evidence

ORD record
ord-0a4c12afa9404e8cb5274b2be83d1704
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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