Sodium Chloride → HCID 14792233, compound

HRID 1613168Notes

Reaction equation

HRID 1613168 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:23]#[N:24].[K+].[Na+].[Cl-].C(=O)([O-])O.[Na+]>CN(C)C=O.CO.C(Cl)(Cl)Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][C:23]#[N:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 10758376Acetamide, 2-chloro-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

Product 1

HCID 14792233HCID 14792233, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.59 g of N-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-chloroacetamide was dissolved in 9 ml of dimethylformamide in accordance with preparation method A, and 637 mg of potassium cyanide was added thereto, followed by stirring at external temperature of 90° C. for 1.5 hours. After the reaction solution was cooled down, saturated NaCl solution was added and extraction was carried out with ethyl acetate and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The thus obtained residue was dissolved in benzene, and then hydrochloric acid-ether solution was added thereto to obtain a deposited oily substance by an inclination method. Then, aqueous saturated sodium hydrogencarbonate solution was added to the thus obtained oily substance and extracted again by ethyl, dried over magnesium sulfate, distilled under reduced pressure to obtain a brown oily substance. This was subjected to silica gel column chromatography (solvent; chloroform:methanol=7:1). 418 mg of light brown oily N-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-cyanoacetamide was obtained.

Workup

  1. additionwas added
  2. temperatureAfter the reaction solution was cooled down
  3. extractionextraction
  4. dry with materialdried over magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. dissolutionThe thus obtained residue was dissolved in benzene
  7. additionhydrochloric acid-ether solution was added
  8. customto obtain a deposited oily substance by an inclination method
  9. extractionextracted again by ethyl
  10. dry with materialdried over magnesium sulfate
  11. distillationdistilled under reduced pressure
  12. customto obtain a brown oily substance

Sources & evidence

ORD record
ord-c2bb3ae61cb64158841d5edb27e06bee
Source dataset
uspto-grants-1993_03
Patent number
US05192774

Reaction notes

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