(+-)-3,4-Dimethoxyamphetamine → 1-[[2-(3,4-Dimethoxyphenyl)-1-methylethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol
Reaction equation
[I:1][C:2]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[CH2:8][O:7]1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][CH:26]([NH2:28])[CH3:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>S1(CCCC1)(=O)=O.CCOCC>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][CH:26]([NH:28][CH2:8][CH:6]([OH:7])[CH2:5][O:4][C:3]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:2]=2[I:1])[CH3:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5.6 g (0.018 mole) of [(2-iodo-5-methoxyphenoxy)methyl]oxirane, the product of Example 5b. and 3.25 g (0.016 mole) of 2-(3,4-dimethoxyphenyl)-alphamethylethylamine in 15 ml of sulfolane was heated at 80° C. for one hour and at 110° for six hours. The mixture was dissolved in ether and the ether washed with water and brine. The ether layer was dried (K2CO3) and the solvent evaporated in vacuo. The residue was flash chromatographed on SiO2 using MeOH:CHCl3, 1:30 as the eluant. The major compound bearing fractions were pooled and the solvent evaporated in vacuo. There was obtained 5.9 g (71% yield) of 1-[[2-(3,4-dimethoxyphenyl)-1-methylethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol as a yellow oil.
Workup
- washthe ether washed with water and brine
- dry with materialThe ether layer was dried (K2CO3)
- customthe solvent evaporated in vacuo
- customchromatographed on SiO2
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-1292f9a889c84aef83f3235d1b0b8fa5
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652584
Reaction notes
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