Propionyl chloride → N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl] propionamide

HRID 847737Notes

Reaction equation

HRID 847737 reaction equation
[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](Cl)(=[O:22])[CH2:20][CH3:21]>N1C=CC=CC=1.O1CCCC1>[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:19](=[O:22])[CH2:20][CH3:21])[CH3:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 130179203-[3-[1-(1-Pyrrolidinyl)ethyl]phenoxy]propylamine

Product 1

HCID 20567148N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl] propionamideYield 71.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

211.8 mg of 3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine was dissolved in 2 ml of dry pyridine, and the solution was stirred under ice cooling. A solution of 87 mg of propionyl chloride in 2 ml of dry tetrahydrofuran was added dropwise in small portions. After the addition, the reaction temperature was adjusted to room temperature, and the mixturwe was stirred for 2 hours. The solvent was distilled off, and 10 ml of water was added. Furthermore, 300 mg of potassium carbonate was added. The precipitated oily product was extracted with 30 ml of chloroform. The extract was dried over anhydrous potassium carbonate, and the solvent was distilled off. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 185 mg of N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl] propionamide as an oil.

Workup

  1. additionAfter the addition
  2. customwas adjusted to room temperature
  3. stirringthe mixturwe was stirred for 2 hours
  4. distillationThe solvent was distilled off
  5. addition10 ml of water was added
  6. additionFurthermore, 300 mg of potassium carbonate was added
  7. extractionThe precipitated oily product was extracted with 30 ml of chloroform
  8. dry with materialThe extract was dried over anhydrous potassium carbonate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by TLC (developing solvent: chloroform/methanol=9/l)

Sources & evidence

ORD record
ord-685308e8f61742aea85e2b9cb3f80335
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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