2-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-ol → N-(2-(4-Methylphenoxy)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

HRID 280320Notes

Reaction equation

HRID 280320 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[CH2:3][NH2:4].[CH3:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](=O)[CH3:23])=[CH:18][CH:17]=1>>[CH3:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH:22]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[CH3:23])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 81195p-Tolyloxyacetone

Product 1

HCID 23322166N-(2-(4-Methylphenoxy)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Procedure

The title compound was prepared in the manner described in Example 3 using 2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine and (4-methylphenoxy)propan-2-one. The residual oil was chromatographed on Kieselgel 60. Elution with 5% methanol-chloroform gave the title compound m.p. 86-96 (heptane). τ(CDCl3) 8.9 (3H, d, J=6 Hz), 7.7 (3H, s), 6.7-7.6 (5H, m, 2H disappears with D2O) 6.0-6.5 (2H, m), 5.3 (1H, m), 3.25 (2H, d, J=9 Hz), 2.95 (2H, d, J=9 Hz), 2.3-2.65 (4H, m).

Workup

  1. customThe title compound was prepared in the manner
  2. customThe residual oil was chromatographed on Kieselgel 60
  3. washElution with 5% methanol-chloroform

Sources & evidence

ORD record
ord-2e1157704a434cdea5f4d0b0a78124fe
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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