2-Methyl-1-(4-methylphenyl)propan-2-amine → N-(2-(4-Methylphenyl)-1,1-dimethylethyl)-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 280314Notes

Reaction equation

HRID 280314 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][C:20]([CH3:23])([CH3:22])[NH2:21])=[CH:15][CH:14]=1>>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C: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)([CH3:22])[CH3:23])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 1164872-Methyl-1-(4-methylphenyl)propan-2-amineHCID 124638932-(3-Chlorophenyl)-2-oxoacetaldehyde

Product 1

HCID 23322165N-(2-(4-Methylphenyl)-1,1-dimethylethyl)-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)-1,1-dimethyl ethanamine. The chromatographed material was recrystallized from cyclohexane to give the title compound m.p. 104-105. τ(CDCL3), 8.9 (6H, s), 7.7 (3H, s), 7.4 (2H, s), 7.1 (2H, dd,), 5.45 (1H, dd), 3.0 (4H, s), 2.5-2.8 (4H, m).

Workup

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

Sources & evidence

ORD record
ord-912c499e94f6447b84ffa84aa2a44160
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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