4-Bromo-1,2-dichlorobenzene → (2RS,3RS)-3-(3,4-dichlorophenyl)-1-dimethylamino-2-methylpentan-3-ol hydrochloride

HRID 1067210Notes

Reaction equation

HRID 1067210 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][CH:4]([CH3:9])[C:5](=[O:8])[CH2:6][CH3:7].Br[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1.[Mg]>>[ClH:18].[Cl:19][C:14]1[CH:13]=[C:12]([C:5]([OH:8])([CH2:6][CH3:7])[CH:4]([CH3:9])[CH2:3][N:2]([CH3:10])[CH3:1])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

4

Reactant 3

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 30487291-(Dimethylamino)-2-methyl-3-pentanoneHCID 5462224Magnesium

Product 1

HCID 18322687(2RS,3RS)-3-(3,4-dichlorophenyl)-1-dimethylamino-2-methylpentan-3-ol hydrochlorideYield 43.7%

Procedure

39 g of crude mixture were prepared analogously to Example 1 from 15 g (105 mmole) 1-dimethylamino-2-methylpentan-3-one, 35.5 g (157 mmole) 4-bromo-1,2-dichlorobenzene and 3.8 g (157 mmole) magnesium turnings. This mixture was introduced on to a 7×40 cm column packed with silica gel and eluted with 4:1 ethyl acetate/methanol. 14.9 g of base were obtained, from which 11.2 g of hydrochloride (2) (31% theoretical) with a melting point of 183-184° C. were obtained with trimethylchlorosilane/water in 2-butanone/diisopropyl ether.

Workup

  1. additionThis mixture was introduced on to a 7×40 cm column
  2. washeluted with 4:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-c2c509eb22c94392b776d4b33f69ca3c
Source dataset
uspto-grants-2001_06
Patent number
US06248737B1

Reaction notes

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