(E)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-hex-3-enyl]-dimethylamine hydrochloride → (E)-(RS)-3-[1-(2-dimethylamino-1-methyl-ethyl)-but-1-enyl]-phenol hydrochloride

HRID 2394982Notes

Reaction equation

HRID 2394982 reaction equation
[Cl:1]CCl.[OH-].[Na+].Cl.C[O:8][C:9]1[CH:10]=[C:11](/[C:15](=[CH:22]/[CH2:23][CH3:24])/[CH:16]([CH3:21])[CH2:17][N:18]([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1>>[ClH:1].[CH3:20][N:18]([CH3:19])[CH2:17][CH:16](/[C:15](/[C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=1)=[CH:22]\[CH2:23][CH3:24])[CH3:21]

Participants

3

Reactant 2

HCID 18974546(E)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-hex-3-enyl]-dimethylamine hydrochlorideHCID 23721229Sodium hydroxide methylene chloride

Product 1

HCID 18974509(E)-(RS)-3-[1-(2-dimethylamino-1-methyl-ethyl)-but-1-enyl]-phenol hydrochlorideYield 86%

Procedure

The base was released with dichloromethane/sodium hydroxide solution from (14), which was prepared as in Example 13, and after drying the solution the dichloromethane was removed by distillation. Hydrochloride (17) was obtained, under the conditions given in Example 2, from the base thus obtained, in a yield of 86% theoretical and with a melting point of 214° C.

Workup

  1. customwas prepared as in Example 13
  2. dry with materialafter drying the solution the dichloromethane
  3. customwas removed by distillation

Sources & evidence

ORD record
ord-65bff384acb5459c9136a849ac102319
Source dataset
uspto-grants-1998_09
Patent number
US05811582

Reaction notes

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