(+-)-3,4-Dimethoxyamphetamine → 3-[3-(3,4-Dimethoxyphenyl)-2-propylamino]1,2-propanediol

HRID 325358

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:15]1[O:17][CH:16]1[CH2:18][OH:19]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:17])[CH2:18][OH:19])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-(3,4-dimethoxyphenyl)-2-propylamine (20.0 g., 0.10 m.) in isopropanol (20 ml.) is heated to 50° C. while a solution of glycidol (5.0 g., 0.067 m.) in isopropanol (5ml.) is added over 15 minutes. The mixture is stirred at 50° C. for 0.5 hours and then at 70° C. for 16 hours. The solvent is concentrated under reduced pressure and the residue is chromatographed on silica gel, eluting with 10% MeOH-CHCl3 saturated with NH3 to yield (I) weighing 14.37 g. (80%).

Workup

additionis added over 15 minutes
waitat 70° C. for 16 hours
concentrationThe solvent is concentrated under reduced pressure
customthe residue is chromatographed on silica gel
washeluting with 10% MeOH-CHCl3 saturated with NH3

Sources & evidence

ORD record: ord-92a35f2d760a45c38edb2edad7e594d5
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440774

Linked notes

Loading…