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

HRID 2394981
Notes
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Reaction equation

HRID 2394981 reaction equation
[Cl:1]CCl.[OH-].[Na+].Cl.C[O:8][C:9]1[CH:10]=[C:11](/[C:15](=[CH:22]/[CH3:23])/[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]\[CH3:23])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 18974531(E)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethylamine hydrochlorideHCID 23721229Sodium hydroxide methylene chloride

Product 1

HCID 18974528(E)-(RS)-3-[1-(2-dimethylamino-1-methyl-ethyl)-propenyl]-phenol hydrochlorideYield 73%

Procedure

The base was released with dichloromethane/sodium hydroxide solution from (5), which was prepared according to Example 5, and after drying the solution dichloromethane was removed by distillation. Hydrochloride (6), which had a melting point of 80° C., was obtained in a yield of 73% theoretical from the base obtained, under the conditions given in Example 2.

Workup

custom
was prepared
  • dry with materialafter drying the solution dichloromethane
  • customwas removed by distillation
  • customwas obtained in a yield of 73% theoretical from the base
  • customobtained, under the conditions
  • Sources & evidence

    ORD record
    ord-1fecc7ddaeca4c5b90458f480067f15b
    Source dataset
    uspto-grants-1998_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05811582

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes