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

HRID 1731573Notes

Reaction equation

HRID 1731573 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]([F: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]([F:23])[CH:18]=2)[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 358002-Amino-1-(3-fluorophenyl)ethan-1-olHCID 4311764Sodium borohydride

Product 1

HCID 20227980N-[2-(4-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-fluorophenyl)ethanamine

Procedure

1-(4-Methoxyphenyl)propan-2-one (2.25 g) and 2-hydroxy-2-(3-fluorophenyl)ethanamine (2.13 g) were condensed ahd subsequently reduced with sodium borohydride (2.75 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-fluorophenyl)ethanamine, mp 85°-9° C., as a 37:63 mixture of diastereoisomers.

Workup

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

Sources & evidence

ORD record
ord-2b38915ea92c4bc7bb59a6862849825d
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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