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

HRID 235670

Reaction equation

HRID 235670 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([NH2:11])(=[O:10])[CH:8]=[CH2:9]>CCO>[O:10]([CH2:6][CH2:5][CH3:4])[CH2:7][CH2:8][CH3:9].[N:1]1([CH2:9][CH2:8][C:7]([NH2:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6579AcrylamideHCID 8082Piperidine

Product 2

HCID 8114Propyl etherHCID 5667843-(Piperidin-1-yl)propanamideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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

Sources & evidence

ORD record
ord-41cfecc7b47843609ffcb8f699a8479d
Source dataset
uspto-grants-1987_02
Patent number
US04640925

Linked notes

Loading…