2-Bromoethanol → 2-{[(1R)-1-phenylethyl]amino}ethan-1-ol

HRID 1069402Notes

Reaction equation

HRID 1069402 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][OH:13]>ClCCl>[OH:13][CH2:12][CH2:11][NH:9][C@H:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

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

Product 1

HCID 69938212-{[(1R)-1-phenylethyl]amino}ethan-1-olYield 76,003%

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-f52640b0735f4828a029802ddd5ff12a
Source dataset
uspto-grants-2001_06
Patent number
US06252076B1

Reaction notes

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