Acetyl chloride → 2-Acetyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 27248Notes

Reaction equation

HRID 27248 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[CH2:15][NH:14][CH2:13][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl>[C:24]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 504718-Phenyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 233443892-Acetyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.2 parts of 8-phenyl-1,2,3,4-tetrahydroisoquinoline and 4 parts of triethylamine in 90 parts by volume of methylene chloride is cooled in an ice bath with stirring and 1.7 part of acetyl chloride in 10 parts by volume of methylene chloride is added slowly. The mixture is allowed to warm to ambient temperature and stirred for about 2 hours. The reaction solution is washed four times with 20 parts by volume portions of water and then dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure to afford 2-acetyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. stirringstirred for about 2 hours
  2. washThe reaction solution is washed four times with 20 parts by volume portions of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-bd168fbdeedf4c7582465d488dfca42c
Source dataset
uspto-grants-1980_09
Patent number
US04220778

Reaction notes

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