Acrylamide → 3-(Piperidin-1-yl)propanamide

HRID 1380904

Reaction equation

HRID 1380904 reaction equation
C(S)(=N)N.[NH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([NH2:15])(=[O:14])[CH:12]=[CH2:13]>CCO>[N:5]1([CH2:13][CH2:12][C:11]([NH2:15])=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 8082PiperidineHCID 178513445HCID 178513445, compound

Product 1

HCID 5667843-(Piperidin-1-yl)propanamideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Carbamimidothioic acid, N'-cyano-N-[3-[4-(diphenylmethylene)-1-piperidinyl]-propyl]-, methyl ester. A solution of piperidine, 4-(diphenylmethylene) (0.10 mole) and acrylamide (8.95 g, 0.062 mole) in EtOH (50 ml) was refluxed overnight. This reaction mixture was filtered and concentrated. The resulting while solid residue was dissolved in CHCl3, washed with H2O (3×150 ml), dried (Na2SO4) and the solvent removed to give thick yellow oil. Crystallization from CH2Cl2 -i-Pr2O afforded 29.01 g (75%) of 1-piperidinepropanamide, 4-(diphenylmethylene)-; mp 105°-7° C.

Workup

  1. filtrationThis reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe resulting while solid residue was dissolved in CHCl3
  4. washwashed with H2O (3×150 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed
  7. customto give thick yellow oil
  8. customCrystallization from CH2Cl2 -i-Pr2O

Sources & evidence

ORD record
ord-1789272e3d394ccf8937f1b06bce883b
Source dataset
uspto-grants-1986_04
Patent number
US04584301

Linked notes

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