2-Amino-1-(3-chlorophenyl)ethan-1-ol → HCID 20556100, compound

HRID 1105620Notes

Reaction equation

HRID 1105620 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)[CH3:26])=[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][CH:25]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[CH3:26])=[CH:22][CH:23]=1)([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 198745324-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one

Product 1

HCID 20556100HCID 20556100, compound

Procedure

This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-chlorophenyl) ethanamine (5.45 g) and 4-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one (7.11 g). The resulting oil was chromatographed on Kieselgel 60. Elution with 5% methanol-chloroform gave the title compound, 9.8 g τ (CDCl3) 8.9 (3H, d, J=6 Hz), 6.8-7.5 (7H, m, 2H disappears with D2O), 6.25 (3H, s), 5.4 (1H, m), 3.6 (1H, d, J=16 Hz), 2.5-2.9 (8H, m), 2.35 (1H, d, J=16 Hz).

Workup

  1. customThis was prepared in an identical manner to the compound
  2. customThe resulting oil was chromatographed on Kieselgel 60
  3. washElution with 5% methanol-chloroform

Sources & evidence

ORD record
ord-e91275953ab24871b3e22f4352ffec10
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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