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

HRID 1074404Notes

Reaction equation

HRID 1074404 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[C:7]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([O:9][CH2:10][CH3:11])=[O:8].C=O.[C:20](=O)=O>O.O1CCOCC1>[C:7]([CH:12]1[CH2:13][CH2:14][N:15]([CH2:20][C:3](=[CH2:4])[C:1]#[N:2])[CH2:16][CH2:17]1)([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 130376092-(4-Carboethoxy-1-piperidylmethyl)propenenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Cyanoacetic acid (8.6 g., 0.1 mole) was dissolved in 35 ml. of dioxane. 4-Carboethoxypiperidine (15.7 g., 0.1 mole) was added--a precipitate rapidly formed. When one-half was added 10 ml. of water was then admixed and the temperature controlled below 24° C. until complete addition. With ice bath cooling, 37% aqueous formaldehyde (18 g., 0.2 mole) was dripped in over an 8-minute period and the temperature allowed to rise to 29° C. accompanied by vigorous carbon dioxide evolution. Two phases separated and stirring was continued for an additional 12 hours. After concentration in a bath at 45° C. and under reduced pressure, 22.4 g. of an oil resulted. The product was distilled, b.p., 130°-132° C./0.6 mm., yield, 16.3 g.

Workup

  1. customa precipitate rapidly formed
  2. additionWhen one-half was added 10 ml
  3. additionthe temperature controlled below 24° C. until complete addition
  4. temperatureWith ice bath cooling
  5. customwas dripped in over an 8-minute period
  6. customto rise to 29° C.
  7. customTwo phases separated
  8. concentrationAfter concentration in a bath at 45° C.
  9. customof an oil resulted
  10. distillationThe product was distilled
  11. custom130°-132° C./0.6 mm
  12. custom, yield

Sources & evidence

ORD record
ord-531e7c4bc2614d47a2f26a0c41416037
Source dataset
uspto-grants-1983_07
Patent number
US04391812

Reaction notes

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