Carbon Dioxide → N-(n-Butyl)-1-(2-cyano-2-propenyl)-4-piperidinecarboxamide

HRID 66654Notes

Reaction equation

HRID 66654 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[CH2:7]([NH:11][C:12](=[O:19])[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:8][CH2:9][CH3:10].C=O.[C:22](=O)=O>C(Cl)(Cl)Cl.CO.O.O1CCOCC1>[CH2:7]([NH:11][C:12]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:22][C:3]([C:1]#[N:2])=[CH2:4])[CH2:15][CH2:14]1)=[O:19])[CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 16228130N-butylpiperidine-4-carboxamide

Product 1

HCID 13041038N-(n-Butyl)-1-(2-cyano-2-propenyl)-4-piperidinecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

Cyanoacetic acid (0.9 g., 0.01 mole) was dissolved in 11 ml. of dioxane and 4 ml. of water. N-butyl isonipecotamide (1.84 g., 0.01 mole) was added with stirring in portions to keep the temperature below 30° C. In 2 minutes 37% aqueous formaldehyde (1.66 g., 0.02 mole) was added and the temperatures maintained at 25°-28° C. Carbon dioxide evolution was evident. After 4 hours, the reaction appeared complete as determined by thin layer chromatography on silica gel developed with chloroform-methyl alcohol (95:5). The solvents were removed by stripping at 35° C./15 mm. and the residue taken up in 100 ml. methylene chloride. The organic phase was washed with water, dried and stripped to yield 1.7 g. of product, analytically pure.

Workup

  1. customthe temperature below 30° C
  2. temperaturethe temperatures maintained at 25°-28° C
  3. customThe solvents were removed
  4. customby stripping at 35° C.
  5. washThe organic phase was washed with water
  6. customdried
  7. customto yield 1.7 g

Sources & evidence

ORD record
ord-fb3dd7bc162e4a3a8b92f48aff9182b8
Source dataset
uspto-grants-1982_08
Patent number
US04342872

Reaction notes

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