Sodium hydride → N,N-Dimethyl-3-[2-(4-phenylbutyl)phenoxy]propylamine

HRID 743172Notes

Reaction equation

HRID 743172 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl>CC(N(C)C)=O>[CH3:21][N:22]([CH2:23][CH2:24][CH2:25][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 125964892-(4-Phenylbutyl)phenol

Product 1

HCID 9904842N,N-Dimethyl-3-[2-(4-phenylbutyl)phenoxy]propylamineYield 67.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

96 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling and stirring, to a solution of 226 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3) in 10 ml of dimethylacetamide, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, 174 mg of 3-dimethylaminopropyl chloride hydrochloride were added, and the reaction mixture was stirred at 70° C. for 14 hours. It was then poured into ice-water, and the aqueous mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The 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 210 mg (yield 67%) of the title compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at 70° C. for 14 hours
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe oily residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-3941d0a0415e4de78743661cd6ab6b80
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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