1-(p-Methoxyphenyl)-2-propanone → N-[2-(4-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-bromophenyl)ethanamine

HRID 1731574Notes

Reaction equation

HRID 1731574 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]([Br: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]([Br:23])[CH:18]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 4311764Sodium borohydrideHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-ol

Product 1

HCID 20227986N-[2-(4-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-bromophenyl)ethanamine

Procedure

1-(4-Methoxyphenyl)propan-2-one (3.10 g) and 2-hydroxy-2-(3-bromophenyl)ethanamine (4.08 g) were condensed and subsequently reduced with sodium borohydride (3.8 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-bromophenyl)ethanamine, mp 79°-83° C., as a 47:53 mixture of diastereoisomers.

Workup

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

Sources & evidence

ORD record
ord-994e83e9ad374ade8f510e3175305381
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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