Formaldehyde → 2-(Piperidin-1-ylmethyl)prop-2-enenitrile
Reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:13]=O>O1CCOCC1>[N:7]1([CH2:13][C:3](=[CH2:4])[C:1]#[N:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Cyanoacetic acid (51 g., 6 mole) was dissolved in 150 ml. of dioxane, the solution cooled to 5° C. and piperidine (53 g., 0.6 mole) dripped in while maintaining the temperature at 10°-15° C. Then, 37% aqueous formaldehyde (109.5 g., 1.35 mole) was slowly added at 0°-10° C. After two hours, the ice bath was removed and the mixture stirred overnight at 20°-25° C. It was then stripped at 15 mm. pressure and bath temperature of 48° C. The residue was chilled, mixed with 100 ml. of ether, saturated with sodium chloride and the ether layer separated. This extract was washed with two 25 ml. portions of cold 5% aqueous potassium carbonate and finally with 10 ml. of ice water. The ether solution was dried over anhydrous magnesium sulfate, filtered, stripped and fractionated using a Vigreux column. The fraction boiling at 86°-88° C./2 mm. was of practically analytical quality, 40.8 g., Rf 0.66 on silica gel using chloroform-methyl alcohol (90:10) development. This is, however, a known compound.
Workup
- temperaturewhile maintaining the temperature at 10°-15° C
- customthe ice bath was removed
- custompressure and bath temperature of 48° C
- temperatureThe residue was chilled
- additionmixed with 100 ml
- customof ether, saturated with sodium chloride and the ether layer separated
- washThis extract was washed with two 25 ml
- dry with materialThe ether solution was dried over anhydrous magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-cd4cd7d8c769455ba21f063724d6d5d3
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04342872
Reaction notes
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