1-(4-Methylphenyl)propan-2-one → N-[2-(4-Methylphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 280299Notes

Reaction equation

HRID 280299 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]([OH:22])[CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=1>C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:21][CH2:20][CH:19]([OH:22])[C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=2)[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1374281-(4-Methylphenyl)propan-2-oneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Product 1

HCID 18628125N-[2-(4-Methylphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamineYield 56.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-methylphenylacetone (1.56 g) and 2-(3-chlorophenyl)-2-hydroxyethanamine (1.81 g) was refluxed in benzene (70 ml) under Dean & Stark conditions for 4 h. The solvent was removed under reduced pressure, replaced with ethanol (100 ml) and the solution hydrogenated using Pt as catalyst. The filtered solution was evaported and the residual oil chromatographed on Kieselgel 60 (150 g). Elution with 1% methanol-chloroform gave the title compound (1.8 g) as an oil. Crystallisation from hexane gave 1.26 g as a 56:44 mixture of diastereoisomers, mp 76-78.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residual oil chromatographed on Kieselgel 60 (150 g)
  3. washElution with 1% methanol-chloroform

Sources & evidence

ORD record
ord-97f3fb3d5c7b49b1b9a707c782c48a7d
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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