3-(Trifluoromethyl)phenylglyoxal → N-(2-(4-Carbomethoxyphenyl)-1,1-dimethylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

HRID 851500Notes

Reaction equation

HRID 851500 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([C:9]([CH:11]=O)=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([CH3:29])([CH3:28])[NH2:27])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16]>>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([NH:27][CH2:11][CH:9]([OH:10])[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)([CH3:28])[CH3:29])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 27832843-(Trifluoromethyl)phenylglyoxalHCID 20134200Methyl 4-(2-amino-2-methylpropyl)benzoate

Product 1

HCID 20501355N-(2-(4-Carbomethoxyphenyl)-1,1-dimethylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

Procedure

The title compound was prepared as in Example 1a from 3-trifluoromethylphenyl glyoxal (2.0 g) and 2-(4-carbomethoxyphenyl)-1,1-dimethyl ethanamine (2.0 g) and crystallised from hexane m.p. 88°-90°. τ(CDCl3) 8.93 (6H,s), 6.8-8.0 (4H,m+2H replaceable by D2O), 6.1 (3H,s), 5.33 (1H,m), 2.8 (2H,d,J=8 Hz), 2.2-2.6 (4H,m), 2.03 (2H,d,J=8 Hz).

Workup

  1. customcrystallised from hexane m.p. 88°-90°

Sources & evidence

ORD record
ord-52b1dc0c52304037a7afecf74c38009d
Source dataset
uspto-grants-1983_05
Patent number
US04385066

Reaction notes

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