Water → 1-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

HRID 2388699Notes

Reaction equation

HRID 2388699 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N:11]1([C:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH:6]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 122563N-Acetyl-4-piperidoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 141055951-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Acetyl-4-piperidinone (1.3 g, 9.2 mmol) was dissolved in toluene (10 ml), and pyrrolidine (0.72 g, 10.13 mmol) and p-toluenesulfonic acid hydrate (catalytic) were added. The reaction mixture was refluxed under an inert gas for 2 hours using a water separator, cooled slowly under an inert gas and concentrated in vacuo and the residue was dried. The crude product was employed immediately without purification. The yield was 1.87 g (>99%).

Workup

  1. temperatureThe reaction mixture was refluxed under an inert gas for 2 hours
  2. temperaturecooled slowly under an inert gas
  3. concentrationconcentrated in vacuo
  4. customthe residue was dried
  5. customThe crude product was employed immediately without purification

Sources & evidence

ORD record
ord-b242d5a21ca146748cdf84529a6bc806
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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