Piperidine → 3-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]prop-2-enenitrile

HRID 1376953Notes

Reaction equation

HRID 1376953 reaction equation
FC(F)(C(F)F)COC1C=CC(C=O)=CC=1.C(CC(O)=O)#N.N1CCCCC1.[F:29][C:30]([F:46])([CH:43]([F:45])[F:44])[CH2:31][O:32][C:33]1[CH:42]=[CH:41][C:36](/[CH:37]=[CH:38]\[C:39]#[N:40])=[CH:35][CH:34]=1.FC(F)(C(F)F)COC1C=CC(/C=C/C#N)=CC=1>N1C=CC=CC=1>[F:29][C:30]([F:46])([CH:43]([F:44])[F:45])[CH2:31][O:32][C:33]1[CH:42]=[CH:41][C:36]([CH:37]=[CH:38][C:39]#[N:40])=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 8082Piperidine2×HCID 9740Cyanoacetic acid2×HCID 10199069HCID 10199069, compoundHCID 117466214-(2,2,3,3-Tetrafluoropropoxy)benzaldehydeHCID 86751210HCID 86751210, compound

Product 1

HCID 534261283-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]prop-2-enenitrileYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 500 g of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde, 183 g of cyanoacetic acid, 250 ml of pyridine and 250 ml of piperidine are heated with stirring and allowed to react for 1 hour at 110° C. A further 36.6 g of cyanoacetic acid are then added and the mixture is allowed to react for a further 30 minutes at 110° C. The reaction mixture is cooled, distilled under reduced pressure and 433.1 g of 4-(2,2,3,3-tetrafluoropropoxy)cinnamonitrile are obtained (yield: 78%; purity 95%) in the form of a mixture of isomers which contains cis-4-(2,2,3,3-tetrafluoropropoxy)cinnamonitrile and trans-4-(2,2,3,3-tetrafluoropropoxy)cinnamonitrile in a molar ratio cis:trans of approximately 1.35 to 1.8:1 (corresponding to a weight ratio of about (58 to 64):(42 to 36)) and in addition up to about 3% by weight of piperidine and 2% by weight of unidentified impurities and resins.

Workup

  1. temperatureare heated
  2. customto react for 1 hour at 110° C
  3. customto react for a further 30 minutes at 110° C
  4. temperatureThe reaction mixture is cooled
  5. distillationdistilled under reduced pressure and 433.1 g of 4-(2,2,3,3-tetrafluoropropoxy)cinnamonitrile
  6. customare obtained (yield: 78%; purity 95%)
  7. additionin the form of a mixture of isomers which

Sources & evidence

ORD record
ord-3f4e799f73404540a977317a0e94f3a6
Source dataset
uspto-grants-1997_09
Patent number
US05663410

Reaction notes

Loading…