Dimethylamine → 1-Methyl-3-phenoxypropyldimethylamine

HRID 464813Notes

Reaction equation

HRID 464813 reaction equation
CO.S(C1C=CC(C)=CC=1)(O[CH:7]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:8])(=O)=O.[CH3:25][NH:26][CH3:27].C(OCC)C>C(Cl)(Cl)Cl>[CH3:8][CH:7]([N:26]([CH3:27])[CH3:25])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 3283Diethyl EtherHCID 133267624-Phenoxy-2-butyl tosylate

Product 1

HCID 201358801-Methyl-3-phenoxypropyldimethylamineYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 60 ml of absolute methyl alcohol were added 10 g of 4-phenoxy-2-butyl tosylate and 5.93 g of dimethylamine. The mixture was reacted in a sealed tube for one hour at 125° C. After the reaction solution was condensed under reduced pressure, 100 ml of diethyl ether was added into the solution and the solution was separated with 20% aqueous sodium hydroxide solution. The ether layer was dried with anhydrous sodium sulfate, and then the ether was removed under reduced pressure therefrom. The residue thus obtained was subjected to an alumina-column chromatography using chloroform as the solvent to give 3.98 g of 1-methyl-3-phenoxypropyldimethylamine in a yield of 66%.

Workup

  1. customThe mixture was reacted in a sealed tube for one hour at 125° C
  2. additionwas added into the solution
  3. customthe solution was separated with 20% aqueous sodium hydroxide solution
  4. dry with materialThe ether layer was dried with anhydrous sodium sulfate
  5. customthe ether was removed under reduced pressure
  6. customThe residue thus obtained

Sources & evidence

ORD record
ord-5ed931f925a74f999e1831b2c914bf3c
Source dataset
uspto-grants-1985_10
Patent number
US04549023

Reaction notes

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