Water → N-[3-(4-(2-Hydroxyethoxy)phenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 851178Notes

Reaction equation

HRID 851178 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[CH2:3][NH2:4].[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=O)[CH3:25])=[CH:18][CH:17]=1.O>C1C=CC=CC=1.CO.ClCCl>[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH:24]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[CH3:25])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 130796444-[4-(2-Hydroxyethoxy)phenyl]butan-2-one

Product 1

HCID 13079635N-[3-(4-(2-Hydroxyethoxy)phenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-hydroxy-2(3-chlorophenyl)ethanamine (2.87 g) and 4-[4-(2-hydroxyethoxy)phenyl]butan-2-one (3.48 g) in benzene (250 ml) was treated under reflux in a Dean and Stark apparatus until water evolution was complete. The solvent was evaporated, the residue dissolved in methanol (200 ml) and cooled in ice. Sodium borohydride (5.3 g) was added in portions over 30 minutes. After a further hour at ambient temperature, the solvent was evaporated and the residue partitioned between water and ethyl acetate. The ethyl acetate layer was dried (MgSO4) and evaporated to give an oil. Chromatography on silica gel in 5% methanol in dichloromethane gave the title compound as a white solid, mp 103°-5° C., as a 39:61 mixture of diastereoisomers.

Workup

  1. additionwas treated
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in methanol (200 ml)
  4. temperaturecooled in ice
  5. additionSodium borohydride (5.3 g) was added in portions over 30 minutes
  6. waitAfter a further hour at ambient temperature
  7. customthe solvent was evaporated
  8. customthe residue partitioned between water and ethyl acetate
  9. dry with materialThe ethyl acetate layer was dried (MgSO4)
  10. customevaporated
  11. customto give an oil

Sources & evidence

ORD record
ord-a63a802c7c954cf4a07dd838327ba545
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

Loading…