1,2-Dibromoethane → (1RS,2RS,4SR)-2-dimethylaminomethyl-1-(3-methylsulphanyl-phenyl)-4-phenethyl-1-cyclohexanol hydrochloride

HRID 2392761Notes

Reaction equation

HRID 2392761 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7]1=[O:20])[CH3:4].Br[C:22]1[CH:27]=[CH:26][CH:25]=[C:24](C)[C:23]=1[SH:29].Br[CH2:31]CBr>CCOCC>[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8][C:7]1([C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([S:29][CH3:31])[CH:22]=1)[OH:20])[CH3:4]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 189804162-Dimethylaminomethyl-4-(phenethyl)-cyclohexanone hydrochlorideHCID 189804692-Bromo-6-methylbenzenethiol

Product 1

HCID 18980474(1RS,2RS,4SR)-2-dimethylaminomethyl-1-(3-methylsulphanyl-phenyl)-4-phenethyl-1-cyclohexanol hydrochlorideYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The base of compound (48) was reacted with 1-bromo-3-methyl-sulphanyl-benzene corresponding to the conditions described in Example 1. In departure from the conditions described in Example 1, ether was used as the solvent and 1,2-dibromoethane was added to the reaction batch in order to increase the yield. The crude product was purified with diisopropyl ether via a silica gel column and was taken up in 2-butanone. After the addition of trimethylchlorosilane/water, compound (51) was obtained in a yield of 23% theoretical.

Workup

  1. additionwas added to the reaction batch in order
  2. temperatureto increase the yield
  3. customThe crude product was purified with diisopropyl ether via a silica gel column
  4. additionAfter the addition of trimethylchlorosilane/water

Sources & evidence

ORD record
ord-7e6918ce28a146e0b062bb9d89088c53
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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