2-Amino-1-(3-chlorophenyl)ethan-1-ol → HCID 44522672, compound

HRID 1105622Notes

Reaction equation

HRID 1105622 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[CH2:3][NH2:4].[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)[CH2:26][CH3:27])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]>>[C:12](/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH:26]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[CH3:27])=[CH:22][CH:23]=1)([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 20556099HCID 20556099, compound

Product 1

HCID 44522672HCID 44522672, compoundYield 22.3%

Procedure

This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-chlorophenyl) ethanamine (1.71 g) and 4-{(E)-2-carbomethoxyethenyl}phenylbutan-2-one (2.32 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound (0.86 g), m.p. 87°-89° C. (hexane) as a 50:50 mixture of diastereoisomers. τ(CDCl3), 8.9 (3H, d, J=6 Hz), 8.15-8.55 (2H, m), 6.9-7.7 (7H, m, 2H disappears with D2O), 6.3 (3H, s), 5.45 (1H, m), 3.65 (1H, d, J=16 Hz), 2.55-2.9 (8H, m), 2.4 (1H, d, J=16 Hz).

Workup

  1. customThis was prepared in an identical manner to the compound
  2. washElution with 1% methanolchloroform on Kieselgel 60

Sources & evidence

ORD record
ord-98d0e5f4d9f74ad48af355231c67cf15
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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