Dimethylamine → 3-Dimethylamino-1-[2-(4-phenylbutyl)phenoxy]-2-propanol

HRID 743171Notes

Reaction equation

HRID 743171 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=2[O:16][CH2:17][CH:18]2[CH2:20][O:19]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH3:1][N:2]([CH3:3])[CH2:20][CH:18]([OH:19])[CH2:17][O:16][C:15]1[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 104931782-[2-(4-Phenylbutyl)phenoxymethyl]oxirane

Product 1

HCID 107612473-Dimethylamino-1-[2-(4-phenylbutyl)phenoxy]-2-propanolYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 ml of 50% by volume aqueous dimethylamine were added to a solution of 19.68 g of 2-[2-(4-phenylbutyl)phenoxymethyl]oxirane [prepared as described in step (a) above] in 300 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature overnight. At the end of this time, the solvent was removed by distillation under reduced pressure, and the pale yellow oily residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 20.6 g (yield 90.4%) of the title compound as a colorless oil.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. customthe pale yellow oily residue was purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-2e8da2c126b84c2ba67ebe76cebcfb4c
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

Loading…