Water → 2-Bromo-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one

HRID 2225812Notes

Reaction equation

HRID 2225812 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.O>ClCCl>[Br:1][CH2:2][C:3]([N:7]1[CH2:8][CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 70461,2,3,4-TetrahydroisoquinolineHCID 89602Bromoacetyl chloride

Product 1

HCID 184672392-Bromo-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetyl chloride (0.25 mL) was added slowly to a cold (5° C.) solution of 1,2,3,4-tetrahydroisoquinoline (0.8 g) in dichloromethane (25 mL) and the mixture was stirred in an ice bath for 45 minutes, then at room temperature overnight. Water (20 mL) was added, the layers were separated and the organic layer was washed in turn with 0.5N hydrochloric acid and sodium bicarbonate solution. The dried extract (MgSO4) was evaporated to provide 0.762 g of 2-(2-bromo-1-oxoethyl)-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customat room temperature
  2. customovernight
  3. customthe layers were separated
  4. washthe organic layer was washed in turn with 0.5N hydrochloric acid and sodium bicarbonate solution
  5. extractionThe dried extract (MgSO4)
  6. customwas evaporated

Sources & evidence

ORD record
ord-4ec210ca128b4e7c9dc3a32a0d6770a7
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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