3-Bromoanisole → (1RS,2RS,4SR)-4-(cyclopentyl-ethyl)-2-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexanol hydrochloride

HRID 2392764Notes

Reaction equation

HRID 2392764 reaction equation
[ClH:1].[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1>>[ClH:1].[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)([OH:15])[CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 169713-BromoanisoleHCID 189804134-(2-Cyclopentyl-ethyl)-2-dimethylaminomethyl-cyclohexanone hydrochloride

Product 1

HCID 67641018(1RS,2RS,4SR)-4-(cyclopentyl-ethyl)-2-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexanol hydrochlorideYield 54%

Procedure

The base of compound (56) was reacted with 1-bromo-3-methoxy-benzene corresponding to the conditions described in Example 1. The base obtained was purified with diisopropyl ether via a silica gel column and was taken up in ether. After adding trimethylchlorosilane/water, compound (52) was obtained in a yield of 54% theoretical.

Workup

  1. customThe base obtained
  2. customwas purified with diisopropyl ether via a silica gel column
  3. additionAfter adding trimethylchlorosilane/water

Sources & evidence

ORD record
ord-de40a689495f477c9d2741d7f3ed9a2a
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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