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

HRID 1074397Notes

Reaction equation

HRID 1074397 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[OH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C=O.[C:16](=O)=O>C(Cl)Cl.O1CCOCC1>[OH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:16][C:3](=[CH2:4])[C:1]#[N:2])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 712Formaldehyde2×HCID 9740Cyanoacetic acidHCID 79341Piperidin-4-ol

Product 1

HCID 130376052-(4-Hydroxy-1-piperidylmethyl)propenenitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Cyanoacetic acid (8.5 g., 0.1 mole) was dissolved in 25 ml. of dioxane. 4-Hydroxypiperidine (10.1 g., 0.1 mole) was added within two minutes; the resultant slurry temperature rose to 33° C. After 1 hour of mixing, 37% aqueous formaldehyde (17 g., 0.2 mole) was run in over a 12 minute period. The temperature rose to 38° C. and carbon dioxide evolved steadily. All was in solution after about one-half of the formaldehyde was added and an additional twelve hours was used to complete the reaction. It was then stripped using a bath at 46° C. and 1-5 mm. of pressure. The residual oil, 17 g., was taken up in methylene chloride, washed with water, dried and stripped to leave 8.1 g. of nearly colorless product, b.p. 125° C./1 mm.

Workup

  1. customrose to 33° C
  2. additionAfter 1 hour of mixing
  3. customwas run in over a 12 minute period
  4. customrose to 38° C.
  5. additionwas added and an additional twelve hours
  6. customthe reaction
  7. customat 46° C.
  8. washwashed with water
  9. customdried
  10. customto leave 8.1 g

Sources & evidence

ORD record
ord-b2dd12ad12054e7ab9e19f82af64d863
Source dataset
uspto-grants-1983_07
Patent number
US04391812

Reaction notes

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