Sodium Cyanide → Ethyl 4-(3-cyanopropyl)-4-cyano-1-piperidinecarboxylate

HRID 1976824Notes

Reaction equation

HRID 1976824 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:16]#[N:17])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1.[C-:18]#[N:19].[Na+]>CN(C)C=O.O>[C:18]([CH2:2][CH2:3][CH2:4][C:5]1([C:16]#[N:17])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:19]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 9838044Ethyl 4-(3-chloropropyl)-4-cyano-1-piperidinecarboxylate

Product 1

HCID 10198845Ethyl 4-(3-cyanopropyl)-4-cyano-1-piperidinecarboxylateYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of ethyl 4-(3-chloropropyl)-4-cyano-1-piperidinecarboxylate (12.7 g) in dimethylformamide (250 ml) was added sodium cyanide (24 g) under nitrogen, with stirring. The mixture was warmed at 140° C. overnight and then cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride solution and water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was chromatographed, eluting with 2:1 heptane/ethyl acetate. The appropriate fractions were collected and concentrated to give 10.8 g (88.5%) of product. A portion was distilled to give the analytical sample, bp196-201° C. (4 mm of mercury).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with saturated sodium chloride solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed
  8. washeluting with 2:1 heptane/ethyl acetate
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-26da19bd1e594714bd02039bc1c1c589
Source dataset
uspto-grants-2001_05
Patent number
US06229014B1

Reaction notes

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