1-(p-Methoxyphenyl)-2-propanone → HCID 18628127, compound

HRID 1731572Notes

Reaction equation

HRID 1731572 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[OH:13][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[CH2:15][NH2:16].[BH4-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:16][CH2:15][CH:14]([OH:13])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydride

Product 1

HCID 18628127HCID 18628127, compound

Procedure

1-(4-Methoxyphenyl)propan-2-one (2.9 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (3.03 g) were condensed and subsequently reduced with sodium borohydride (3.55 g) by an analogous procedure to that described in Example 1. The crude product was recrystallised from diethyl ether-hexane to give N-[2-(4-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine, mp 80°-7° C., as a 45:55 mixture of diastereoisomers.

Workup

  1. customcondensed
  2. customThe crude product was recrystallised from diethyl ether-hexane

Sources & evidence

ORD record
ord-3ef183f0f6c440d2ae3d0c34814dac0e
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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