(+-)-3,4-Dimethoxyamphetamine → 1-[[2-(3,4-Dimethoxyphenyl)-1-methylethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol

HRID 1906509노트

반응식

HRID 1906509 반응식
[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]

참가 물질

5

반응물 2

HCID 8423(+-)-3,4-DimethoxyamphetamineHCID 20212121[(2-Iodo-5-methoxyphenoxy)methyl]oxirane

생성물 1

HCID 202121341-[[2-(3,4-Dimethoxyphenyl)-1-methylethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol수율 73.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 31347Sulfolane용매

실험 절차

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.

후처리

  1. washthe ether washed with water and brine
  2. dry with materialThe ether layer was dried (K2CO3)
  3. customthe solvent evaporated in vacuo
  4. customchromatographed on SiO2
  5. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-1292f9a889c84aef83f3235d1b0b8fa5
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652584

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