p-Methylphenethylamine → N-(2-(4-Methylphenyl)ethyl)-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 280311Notes

Reaction equation

HRID 280311 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH:10]=O)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=1>>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][CH2:10][CH:8]([OH:9])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 76751p-MethylphenethylamineHCID 124638932-(3-Chlorophenyl)-2-oxoacetaldehyde

Product 1

HCID 23322163N-(2-(4-Methylphenyl)ethyl)-2-hydroxy-2-(3-chlorophenyl)ethanamine

Procedure

The title compound was prepared in the manner described in Example 9 using 3-chlorophenylglyoxal and 2-(4-methylphenyl)ethanamine. Recrystallization of the chromatographed material from cyclohexane gave the title compound m.p. 85-88 (analysed as the hemi-hydrate). τ(CDCl3) 7.7 (3H, s), 7.0-7.5 (6H, m, +2H disappears with D2O), 5.4 (1H, dd), 2.9 (4H, s), 2.6-2.8 (4H, m).

Workup

  1. customThe title compound was prepared in the manner
  2. customRecrystallization of the chromatographed material from cyclohexane

Sources & evidence

ORD record
ord-43a6858edb474264a9a6913d44a86668
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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