4-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one → N-{2-(4-{(E)-2-Carbomethoxyethenyl}-phenyl)-1-methylethyl}-2-hydroxy-2-(3-bromophenyl)ethanamine

HRID 1105625Notes

Reaction equation

HRID 1105625 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br: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]([Br:11])[CH:6]=2)[CH3:26])=[CH:22][CH:23]=1)([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 198745324-{(E)-2-carbomethoxyethenyl}phenylpropan-2-oneHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-ol

Product 1

HCID 20556112N-{2-(4-{(E)-2-Carbomethoxyethenyl}-phenyl)-1-methylethyl}-2-hydroxy-2-(3-bromophenyl)ethanamineYield 38.3%

Procedure

This was prepared in an identical manner to the compound described in Example 1 using 2-hydroxy-2-(3-bromophenyl) ethanamine (2.16 g) and 4-{(E)-2-carbomethoxyethenyl}phenylpropan-2-one (2.18 g). Elution with 1% methanolchloroform on Kieselgel 60 gave the title compound as a solid 1.6 g (benzene-petrol 80-100) m.p. 105°-111° C. as a 42:58 mixture of diastereoisomers. τ(CDCl3) 8.95 (3H, d, J=6 Hz), 6.9-7.7 (7H, m, 2H disappears with D2O), 6.2 (3H, s), 5.5 (1H, m), 3.6 (aH, d, J=16 Hz) 2.55 (8H, m), 2.35 (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-fb8ddf9a234544019273f6c9353d55fc
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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