Piperidine → HCID 20327618, compound

HRID 918348Notes

Reaction equation

HRID 918348 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][S:9]([O-:12])(=[O:11])=[O:10].[CH3:13][N+:14]1[N:15]([CH3:26])[C:16](Cl)=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:7][O:8][S:9]([O-:12])(=[O:11])=[O:10].[CH3:26][N+:15]1[N:14]([CH3:13])[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][C:16]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12665764HCID 12665764, compound

Product 1

HCID 20327618HCID 20327618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine (2.56 g, 0.03 mole) is added to 1,2-dimethyl-3-chloro-5-phenylpyrazolium methyl sulfate (4.77 g, 0.015 mole) in absolute ethanol (30 ml) and the mixture stirred with a bar magnet and heated under reflux for 4 hours. After cooling, the reaction mixture is evaporated under reduced pressure to a brown oil, and then dissolved in 50 ml of aqueous saturated sodium bicarbonate solution. The aqueous layer is extracted with ether and this organic layer discarded, then with chloroform (3×100 ml). Evaporation of the chloroform layer affords 1,2-dimethyl-3-phenyl-5-piperidinopyrazolium methyl sulfate as a viscous oil. The oil is redissolved in water and saturated aqueous potassium iodide solution is added. (Sodium iodide is also equally effective). An immediate copious white precipitate of 1,2-dimethyl-3-phenyl-5-piperidinopyrazolium iodide is formed, then filtered and washed with ice cold water to give 3.37 g, (56%) of product mp 179°C to 180°C. The melting point is unchanged by dissolving in chloroform, filtering and reprecipitating with diethyl ether and filtering off the solid. For analysis see Table I, compound 1.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture is evaporated under reduced pressure to a brown oil
  5. dissolutiondissolved in 50 ml of aqueous saturated sodium bicarbonate solution
  6. extractionThe aqueous layer is extracted with ether
  7. customEvaporation of the chloroform layer

Sources & evidence

ORD record
ord-c37ac212c7ea43c8b00c4bb24c1bf00b
Source dataset
uspto-grants-1976_07
Patent number
US03970754

Reaction notes

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