Piperidine → HCID 53775915, compound

HRID 1376954Notes

Reaction equation

HRID 1376954 reaction equation
[F:1][C:2]([F:16])([CH:13]([F:15])[F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.C([CH2:19][C:20]([OH:22])=[O:21])#N.FC(F)(C(F)F)COC1C=CC(/C=C\C#N)=CC=1.N1CCCCC1>N1C=CC=CC=1.C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:16])([CH:13]([F:15])[F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:19][C:20]([OH:22])=[O:21])=[CH:7][CH:6]=1

Participants

7

Reactant 4

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

Product 1

HCID 53775915HCID 53775915, compoundYield 135.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

735.0 g (3.12 mol) of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde, 269 g of cyanoacetic acid, 660 g of cis-4-(2,2,3,3-tetrafluoropropoxy)cinnamonitrile (main fractions containing 80 to 85% by weight of cis isomer) are admixed with 750 g of xylene, 750 ml of pyridine and 750 ml of piperidine and heated to 110° C. with stirring. The mixture is allowed to react for 2 hours, and 53.8 g of cyanoacetic acid are added again and the mixture is allowed to react for a further 30 minutes. After cooling, the reaction mixture is distilled under reduced pressure and 1173 g of 4-(2,2,3,3-tetrafluoropropoxy)cinnamic acid (yield: 87% purity>95% by weight) are obtained 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 of about 1.8:1 and , in addition, about 3% by weight of piperidine and up to 2% by weight of unidentifiable impurities.

Workup

  1. customto react for 2 hours
  2. customto react for a further 30 minutes
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-abbed812b6b043ee804c2b60f84720dc
Source dataset
uspto-grants-1997_09
Patent number
US05663410

Reaction notes

Loading…