1-(4-Methylphenyl)propan-2-one → N-(2-(4-Methylphenyl)-1-methylethyl)-2-hydroxy-2-(3-ethylphenyl)ethanamine

HRID 280321Notes

Reaction equation

HRID 280321 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[CH:6]=1)[CH2:3][NH2:4].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](=O)[CH3:22])=[CH:16][CH:15]=1>>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[CH:6]=2)[CH3:22])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 1374281-(4-Methylphenyl)propan-2-oneHCID 186278602-Amino-1-(3-ethylphenyl)ethan-1-ol

Product 1

HCID 23322150N-(2-(4-Methylphenyl)-1-methylethyl)-2-hydroxy-2-(3-ethylphenyl)ethanamine

Procedure

The title compound was prepared as described in Example 3 using 2-hydroxy-2-(3-ethylphenyl)ethanamine and (4-methylphenyl)propanone. The residual oil was chromatographed on Kieselgel 60. Elution with 2% methanolchloroform gave the title compound, isolated as the hydrochloride salt, as a 54:46 mixture of diastereoisomers m.p. 97-104. τ(d6DMSO) 8.85 (3H, d, J=6 Hz), 8.8 (3H, d, J=6 Hz), 7.7 (3H, s), 7.4 (2H, q, =6 Hz), 6.3-7.2 (5H, m), 4.9 (1H, m), 3.8 (1H, broad, disappears with D2O), 2.8 (4H, s), 2.6-2.8 (4H, m), 1.1+0.2 (2H, broad, both disappear with D2O).

Workup

  1. customThe title compound was prepared
  2. customThe residual oil was chromatographed on Kieselgel 60
  3. washElution with 2% methanolchloroform

Sources & evidence

ORD record
ord-b93a16a56f894b00bfdc0326656e3d97
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

Loading…