Methanol → 1-Methyl-3-phenoxypropyldiethylamine

HRID 580110Notes

Reaction equation

HRID 580110 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.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26].C(OCC)C>C(Cl)(Cl)Cl>[CH3:8][CH:7]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 8021DiethylamineHCID 133267624-Phenoxy-2-butyl tosylate

Product 1

HCID 135201021-Methyl-3-phenoxypropyldiethylamineYield 77%

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 9.62 g of diethylamine. 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 then the solution was separated into the diethyl ether solution and 20% aqueous sodium hydroxide solution. The ether layer was dried over anhydrous sodium sulfate, and the ether was removed under reduced pressure therefrom. The residue thus obtained was subjected to an alumina-column chromatography using chloroform as the developing solvent to give 5.32 g of 1-methyl-3-phenoxypropyldiethylamine in a yield of 77%.

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 into the diethyl ether solution and 20% aqueous sodium hydroxide solution
  4. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  5. customthe ether was removed under reduced pressure
  6. customThe residue thus obtained

Sources & evidence

ORD record
ord-af7033e3d8b043d6a24b41620c1c9924
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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