Water → HCID 18627966, compound

HRID 1731570Notes

Reaction equation

HRID 1731570 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[OH:12][CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[CH2:14][NH2:15].O>C1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:15][CH2:14][CH:13]([OH:12])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 18627966HCID 18627966, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-hydroxyphenyl)propan-2-one (4.6 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (5.2 g) in dry benzene (150 ml) was heated under reflux using a Dean and Stark head until the required amount of water had been collected. The solution was cooled, the solvent evaporated, the residue dissolved in methanol (20 ml), cooled in ice and treated portionwise with sodium borohyride (6.1 g) over 30 minutes. The mixture was stirred for 40 minutes, and the solvent removed under reduced pressure. Water was added to the residue and the mixture adjusted to pH 5 by addition of acetic acid followed by extraction with ethyl acetate. The extracts were washed with water, aqueous sodium bicarbonate and brine, dried (magnesium sulphate), filtered and evaporated to dryness. Chromatography of the residue on silica gel in 5% methanoldichloromethane gave N-[2-(4-hydroxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine mp 50°-5° C., of analytical purity as a 53:47 mixture of diastereoisomers.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customhad been collected
  4. temperatureThe solution was cooled
  5. customthe solvent evaporated
  6. dissolutionthe residue dissolved in methanol (20 ml)
  7. temperaturecooled in ice
  8. additiontreated portionwise with sodium borohyride (6.1 g) over 30 minutes
  9. customthe solvent removed under reduced pressure
  10. additionWater was added to the residue
  11. additionthe mixture adjusted to pH 5 by addition of acetic acid
  12. extractionfollowed by extraction with ethyl acetate
  13. washThe extracts were washed with water, aqueous sodium bicarbonate and brine
  14. dry with materialdried (magnesium sulphate)
  15. filtrationfiltered
  16. customevaporated to dryness

Sources & evidence

ORD record
ord-cb78e80089db4e13bce391c6a3ad0ae5
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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