1-Bromo-3-chlorobenzene → (2RS,3RS)-3-(3-chlorophenyl)-1-dimethylamino-2-methylpentan-3-ol hydrochloride

HRID 1699105Notes

Reaction equation

HRID 1699105 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][CH:15]=[C:14]([Cl:18])[CH:13]=1.[Mg]>>[ClH:18].[Cl:18][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][CH:15]=1

Participants

4

Reactant 3

HCID 79281-Bromo-3-chlorobenzeneHCID 30487291-(Dimethylamino)-2-methyl-3-pentanoneHCID 5462224Magnesium

Product 1

HCID 18322695(2RS,3RS)-3-(3-chlorophenyl)-1-dimethylamino-2-methylpentan-3-ol hydrochlorideYield 19%

Procedure

63 g of crude mixture were obtained under the conditions cited for Example 1 from 38.0 g (270 mmole) 1-dimethylamino-2-methylpentan-3-one, 74.7 g (390 mmole) 1-bromo-3-chlorobenzene and 9.50 g (390 mmole) magnesium turnings. This mixture was introduced on to a 7×45 cm column packed with silica gel and eluted with 7:1 diisopropyl ether/methanol. 12.8 g of base were obtained, from which 10.8 g of hydrochloride (4) (14% theoretical) with a melting point of 160-162° C. were obtained with trimethylchlorosilane/water in 2-butanone/ether.

Workup

  1. additionThis mixture was introduced on to a 7×45 cm column
  2. washeluted with 7:1 diisopropyl ether/methanol

Sources & evidence

ORD record
ord-121ee4b9e0f94c54a3daf9fccd726580
Source dataset
uspto-grants-2002_02
Patent number
US06344558B1

Reaction notes

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