Acetonitrile → 1-Methyl-1-phenyl-2-allyl-1,2,3,4-tetrahydroisoquinoline

HRID 345857

Reaction equation

HRID 345857 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](Br)[CH:18]=[CH2:19].[C:21](#N)C>>[CH3:21][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[CH2:17][CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7841Allyl bromideHCID 6099261-Phenyl-3,4-dihydroisoquinoline

Product 1

HCID 149989201-Methyl-1-phenyl-2-allyl-1,2,3,4-tetrahydroisoquinoline

Procedure

A solution of 1-phenyl-3,4-dihydroisoquinoline (1.0 g) and allyl bromide (0.44 ml) in acetonitrile (10 ml) was refluxed for 2 hours. After cooling it to room temperature, the solvent was evaporated in vacuo and then the residue was stirred in diethyl ether (15 ml) at room temperature. To the mixture was added 3M diethyl ether solution of methylmagnesium bromide (2.0 ml). After 1 hour, the mixture was poured into aqueous ammonium chloride solution. The organic layer was washed with water, sodium chloride aqueous solution and dried over magnesium sulfate, and evaporated in vacuo to give 1-methyl-1-phenyl-2-allyl-1,2,3,4-tetrahydroisoquinoline (0.7 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionTo the mixture was added 3M diethyl ether solution of methylmagnesium bromide (2.0 ml)
  3. additionthe mixture was poured into aqueous ammonium chloride solution
  4. washThe organic layer was washed with water, sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-831d78d385f44fa89665814fbae96128
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Linked notes

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