Water → 1-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol

HRID 1906507Notes

Reaction equation

HRID 1906507 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.[CH2:15]([NH2:27])[CH2:16][C:17]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=1.O>S1(CCCC1)(=O)=O>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][NH:27][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])[CH:26]=[CH:25][C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 8421HomoveratrylamineHCID 20212121[(2-Iodo-5-methoxyphenoxy)methyl]oxirane

Product 1

HCID 138235441-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A solution of 5.0 g (0.016 mole) of [(2-iodo-5-methoxyphenoxy)methyl]oxirane, the product of Example 5b. and 3.25 g (0.0179 mole) of homoveratrylamine in 10 ml of sulfolane was heated at 60°-70° C. for 18 hr. Water was added and the precipitate which formed was collected by filtration. It was recrystallized from acetonitrile to give 7.0 g (87% yield) of crystalline 1-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-(2-iodo-5-methoxyphenoxy)-2-propanol, mp 83°-88° C.

Workup

  1. customthe precipitate which formed
  2. filtrationwas collected by filtration
  3. customIt was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-ebf304384cc94675b808c8cae72c3229
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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