Sodium Cyanide → Ethyl 4-(3-cyanopropyl)-4-cyano-1-piperidinecarboxylate
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
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, bp 196-201° C. (4 mm of mercury).
Workup
- temperaturecooled to ambient temperature
- extractionextracted with ethyl acetate
- washThe organic extracts were washed with saturated, sodium chloride solution and water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customThe residue was chromatographed
- washeluting with 2:1 heptane/ethyl acetate
- customThe appropriate fractions were collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-07de8a92a23e43a2863ecaaa92e147dc
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479501B2
Reaction notes
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