Methanol → 4-[[2-(3,4,5-Trimethoxyphenyl)ethyl](methyl)amino]hexan-3-ol

HRID 232280

Reaction equation

HRID 232280 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9](OC)[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1.[CH2:17]([CH:19]1[CH:21]([CH2:22][CH3:23])[O:20]1)[CH3:18].[CH3:24][OH:25]>>[CH3:24][O:25][C:9]1[CH:10]=[C:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH:21]([CH2:22][CH3:23])[CH:19]([OH:20])[CH2:17][CH3:18])[CH:6]=[C:7]([O:15][CH3:16])[C:8]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1382642,3-DiethyloxiraneHCID 138365N-Methylmescaline

Product 1

HCID 200313814-[[2-(3,4,5-Trimethoxyphenyl)ethyl](methyl)amino]hexan-3-ol

Procedure

Combine 22.5 g (0.1 mol) of N-methyl-3,4,5-trimethoxybenzeneethanamine and 10 g (0.1 mol) of 2,3-diethyloxirane in 150 mL of 90% aqueous methanol. Heat the reaction at 50° C. and follow the progress of the reaction by thin-layer chromatography. At the completion of the reaction remove the solvent in vacuo and chromatograph the residue on silica gel to obtain the title compound.

Workup

  1. temperatureHeat
  2. customthe reaction at 50° C.
  3. customthe progress of the reaction by thin-layer chromatography
  4. customAt the completion of the reaction remove the solvent in vacuo and chromatograph the residue on silica gel

Sources & evidence

ORD record
ord-9557d6b1d5794e29856206cf104fc55c
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

Loading…