Methanol → 1-Methyl-3-phenoxypropyldiethylamine

HRID 464811Notes

Reaction equation

HRID 464811 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 the solution was separated with 20% aqueous sodium hydroxide solution. The ether layer was dried with anhydrous sodium sulfate, and the ether was removed under reduced pressure therefrom. The residue thus obtained was subjected to alumina-column chromatography using chloroform as the 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 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-c0f668ad448447cbba3fa49b9ba6c15e
Source dataset
uspto-grants-1985_10
Patent number
US04549023

Reaction notes

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