Acetophenone → 1-(1-Phenylvinyl)pyrrolidine

HRID 430632Notes

Reaction equation

HRID 430632 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>CCOCC>[C:4]1([C:1]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH2:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 31268Pyrrolidine

Product 1

HCID 5990851-(1-Phenylvinyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
500 °C

Procedure

100 g of molecular sieve are heated at 500° C. for 8 hours and then added to a mixture of 20 mmol of acetophenone and 22 mmol of pyrrolidine in 200 ml of anhydrous ether. The reaction mixture is stirred at ambient temperature until, in the infra-red, no more free ketone (C═O 1689 cm31 1) is detected in the supernatant and the absorption for the enamine (C═C—N 1600 cm−1) is at a maximum. The mixture is then filtered and the molecular sieve is washed with ether. The solvent is evaporated off under reduced pressure and the crude residue is purified by distillation under reduced pressure.

Workup

  1. customthe absorption for the enamine (C═C—N 1600 cm−1)
  2. filtrationThe mixture is then filtered
  3. washthe molecular sieve is washed with ether
  4. customThe solvent is evaporated off under reduced pressure
  5. distillationthe crude residue is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-5c046363a6c84406a11100db0a56f970
Source dataset
uspto-grants-2001_11
Patent number
US06323220B1

Reaction notes

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