Carbon Dioxide → 2-(4-Fluoro-1-piperidylmethyl)propenenitrile

HRID 66649

Reaktionsgleichung

Reaktionsgleichung von HRID 66649
[F:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([CH2:10][C:11](O)=O)#[N:9].[C:14](=O)=O.C(=O)(O)[O-].[Na+]>O.O1CCOCC1>[F:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:14][C:10](=[CH2:11])[C:8]#[N:9])[CH2:4][CH2:3]1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 9740Cyanoacetic acidHCID 516892Sodium BicarbonateHCID 27591594-Fluoropiperidine

Produkt 1

HCID 130410342-(4-Fluoro-1-piperidylmethyl)propenenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

4-Fluoropiperidine (0.7 g., 0.005 mole) was dissolved in a mixture of 3 ml. of dioxane and 2 ml. of water containing cyanoacetic acid (0.43 g., 0.005 mole). The solution was heated to 65° C. and carbon dioxide evolution began. It was maintained at 60°-65° C. for 21/2 hours and allowed to stand overnight. A solid gummy residue, 1 gm., was obtained upon stripping in a bath at 55° C. and at 1 mm. It was taken up in a small amount of water, made alkaline with sodium bicarbonate and extracted with ether. The organic layer was water washed and dried over anhydrous sodium sulfate. After solvent stripping, the product was obtained as a colorless oil, 0.7 g., of analytical purity.

Aufarbeitung

  1. temperatureIt was maintained at 60°-65° C. for 21/2 hours
  2. custom, was obtained
  3. customupon stripping in a bath at 55° C. and at 1 mm
  4. extractionextracted with ether
  5. washwashed
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter solvent stripping, the product was obtained as a colorless oil, 0.7 g

Quellen und Nachweise

ORD-Eintrag
ord-74e54ba5eb154ef3b5f40bb5afe8d738
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342872

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