Piperidine → p-Toluenesulfonic acid

HRID 1992239Notes

Reaction equation

HRID 1992239 reaction equation
N1([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)CCCCC1.[C:12]1(=O)[CH2:16]CCC1.N1CCCCC1.[S:24]([O-])([O-:27])(=[O:26])=[O:25].[Mg+2]>O.CCCCCC>[C:9]1([CH3:8])[CH:10]=[CH:11][C:7]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:12][CH:16]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8452CyclopentanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 137114Piperidine, 1-(1-cyclopenten-1-yl)-

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

1-piperidino-1-cyclopentene was-synthesized as follows. In a 1-L 3-necked round-bottom flask equipped with an overhead stirrer, 20.0 g cyclopentanone was added to 120 mL hexane. 18.43 g piperidine was then added to the solution. 38.0 g anhydrous magnesium sulfate was then added to scavenge the water produced in the reaction, and 0.25 g p-toluenesulfonic acid was added as a catalyst. The mixture was then refluxed with overhead stirring over the course of 4 days. The suspension was allowed to cool, and the magnesium salts were removed by filtration. The hexane solution was then rotoevaporated at about 77° C. and 60 torr in order to remove the hexane solvent and unreacted piperidine.

Workup

  1. customIn a 1-L 3-necked round-bottom flask equipped with an overhead stirrer

Sources & evidence

ORD record
ord-2eab22ec25f54d6b844a73cfb7fa289d
Source dataset
uspto-grants-2010_01
Patent number
US07648694B2

Reaction notes

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