2-Bromoethanol → (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1604030Notes

Reaction equation

HRID 1604030 reaction equation
[CH3:1][C@@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][CH2:12]O>ClCCl>[CH3:1][C@@H:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:12][CH2:11][NH:9]1

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 11084033(R)-1-Methyl-1,2,3,4-tetrahydroisoquinolineYield 85,303.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
51 °C

Procedure

51.45 g(0.43 mmole) of (R)-(+)-α-methylbenzylamine was dissolved in 52 ml of dichloromethane and 63.78 g(0.51 mmole) of 2-bromoethanol was added thereto. This mixture was stirred at 51° C. for 50 hours to complete the reaction. The reaction solution was concentrated under reduced pressure and the residue was subjected to fractional distillation to obtain 54 g of the title compound having pale yellow color.

Workup

  1. customthe reaction
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. distillationthe residue was subjected to fractional distillation

Sources & evidence

ORD record
ord-df70338bc03e4c9dbabd52dcb029ba68
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

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