Phenylglyoxal → N-(2-(4-Methylphenyl)-1,1-dimethylethyl)-2-hydroxy-2-phenyl ethanamine

HRID 280315Notes

Reaction equation

HRID 280315 reaction equation
[C:1]1([C:7]([CH:9]=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[NH2:20])=[CH:14][CH:13]=1>>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:20][CH2:9][CH:7]([OH:8])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([CH3:21])[CH3:22])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 14090PhenylglyoxalHCID 1164872-Methyl-1-(4-methylphenyl)propan-2-amine

Product 1

HCID 23322178N-(2-(4-Methylphenyl)-1,1-dimethylethyl)-2-hydroxy-2-phenyl ethanamine

Procedure

The title compound was prepared in the manner described in Example 9 using phenylglyoxal and 2-(4-methylphenyl)-1,1-dimethylethanamine. The chromatographed material was recrystallized from cyclohexane to give the title compound m.p. 137. τ(CDCl3 +d6DMSO) 8.95 (6H, s), 7.7 (3H, s), 7.35 (2H, s), 7.0-7.3 (2H, dd), 5.3 (1H, dd), 2.9 (4H, s), 2.5-2.7 (5H, m).

Workup

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

Sources & evidence

ORD record
ord-2ffb7ddc52b84b30a66e254974a4796b
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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