Cyclohexylpyrrolidinium hydrochloride salt → 1-Cyclohexylpyrrolidine

HRID 1504901Notes

Reaction equation

HRID 1504901 reaction equation
Cl.[CH:2]1([NH+:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>O>[CH:2]1([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 131733292Cyclohexylpyrrolidinium hydrochloride salt

Product 1

HCID 1390641-Cyclohexylpyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In some instances when some unreacted cyclohexanone is still in the reaction mixture, the product after hydrogenation was purified by adding 3M HCl solution to the mixture (after filtering out the palladium/carbon catalyst) and left to stir for 15-20 minutes. The resulting mixture is then extracted with diethyl ether to remove the cyclohexanone from the mixture and leaving behind the cyclohexylpyrrolidinium hydrochloride salt. The water layer containing cyclohexylpyrrolidinium hydrochloride salt is separated and then neutralized with NaOH solution to a pH of 9-10. The free cyclohexylpyrrolidine is extracted with ethyl acetate, dried over MgSO4 and concentrated on a rotary evaporator at reduced pressure to give the desired product free from any impurities.

Workup

  1. customis separated
  2. extractionThe free cyclohexylpyrrolidine is extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated on a rotary evaporator at reduced pressure

Sources & evidence

ORD record
ord-cc4a1ac6af0c473b86ed423240eb882b
Source dataset
uspto-grants-2015_12
Patent number
US09216911B2

Reaction notes

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