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

HRID 553419Notes

Reaction equation

HRID 553419 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.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[N:11]1([C:7]2[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH:8]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 122563N-Acetyl-4-piperidone

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.95 mL (40 mmol) of 1-acetyl-4-piperidinone, 3.64 mL (44 mmol) of pyrrolidine, 15 mL of toluene and a catalytic quantity of p-toluenesulfonic acid was heated for 12 h with refluxing on a water separator. After removal of the solvent under a vacuum, 7.7 g (99% of theoretical) of the desired product 1-(4-pyrrolidin-1-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (A) were obtained in the form of a brown-red oil.

Workup

  1. customAfter removal of the solvent under a vacuum, 7.7 g (99% of theoretical) of the desired product 1-(4-pyrrolidin-1-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (A)
  2. customwere obtained in the form of a brown-red oil

Sources & evidence

ORD record
ord-874bc4b2fca14bffad4e143260e7824a
Source dataset
uspto-grants-2011_11
Patent number
US08048879B2

Reaction notes

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