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

HRID 126837

Reaction equation

HRID 126837 reaction equation
[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=O.[C:16](=O)=O.C(=O)(O)[O-].[Na+]>O.O1CCOCC1>[F:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:16][C:10](=[CH2:11])[C:8]#[N:9])[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 516892Sodium BicarbonateHCID 27591594-Fluoropiperidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

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). Then, 0.85 g. (0.01 mole) of 37% aqueous formaldehyde was added to the solution. 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.

Workup

  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

Sources & evidence

ORD record
ord-bbf5626a65f8497384b49ee61d97e8ac
Source dataset
uspto-grants-1981_03
Patent number
US04254131

Linked notes

Loading…