1-Phenethylamine → 1-Methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1604024Notes

Reaction equation

HRID 1604024 reaction equation
[CH3:1][CH: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][CH: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 74081-PhenethylamineHCID 108982-Bromoethanol

Product 1

HCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
52 °C

Procedure

103.08 g(0.86 mole) of α-methylbenzylamine was dissolved in 110 ml of dichloromethane and 127.56 g(1.02 mole) of 2-bromoethanol was added thereto. This mixture was stirred at 52° 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 109 g of the title compound, which had a 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-71ef3356f4e640bfbd3b1f2ff1d7ce0b
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

Loading…