3-(Trifluoromethyl)phenylglyoxal → N-(2-(4-Carbomethoxyphenyl)ethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

HRID 851502Notes

Reaction equation

HRID 851502 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][CH2:26][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][CH2:26][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)=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 27832843-(Trifluoromethyl)phenylglyoxalHCID 11183521Methyl 4-(2-aminoethyl)benzoate

Product 1

HCID 15087214N-(2-(4-Carbomethoxyphenyl)ethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

Procedure

The title compound was prepared as in Example 1a from 3-trifluoromethylphenyl glyoxal (3.85 g) and 2-(4-carbomethoxyphenyl) ethanamine (3.4 g), and crystallised from hexane m.p. 75-77.5. τ(CDCl3) 7.66 (2H, broad, replaceable by D2O), 5.9-6.5 (6H, m), 6.15 (3H,s), 5.3 (1H,m), 2.75 (2H,d,J=8 Hz), 2.3-2.6 (4H,m), 2.03 (2H,d,J=8 Hz).

Workup

  1. customcrystallised from hexane m.p. 75-77.5

Sources & evidence

ORD record
ord-2645174f3d6c4fa9a1cd8fa504fc1552
Source dataset
uspto-grants-1983_05
Patent number
US04385066

Reaction notes

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