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

HRID 553417Notes

Reaction equation

HRID 553417 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1(C)C=CC=CC=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1>[N:18]1([C:7]2[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH:8]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

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 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

In stage 1, the compound 1-acetyl-4-piperidinone is reacted in a reaction medium, preferably selected from the group consisting of toluene and benzene, with pyrrolidine in the presence of a catalytic quantity of an acid, preferably in the presence of p-toluenesulfonic acid, with refluxing on a water separator to yield the compound 1-(4-pyrrolidin-1-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (A).

Sources & evidence

ORD record
ord-38c40b642d27481dbd3b111be1f93ccf
Source dataset
uspto-grants-2011_11
Patent number
US08048879B2

Reaction notes

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