Carbon Dioxide → 2-[(4-t-Butyl-1-piperidyl)methyl]propenenitrile

HRID 126839

Reaction equation

HRID 126839 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[C:7]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8].C=O.[C:19](=O)=O>CCOCC.O1CCOCC1>[C:7]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:19][C:3](=[CH2:4])[C:1]#[N:2])[CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 74661Piperidine, 4-(1,1-dimethylethyl)-

Product 1

HCID 130410352-[(4-t-Butyl-1-piperidyl)methyl]propenenitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Cyanoacetic acid (1.75 g., 0.02 mole) was dissolved in 10 ml. of dioxane. In a five minute period 4-t-butylpiperidine (2.8 g., 0.02 mole) was added, the temperature rose to 25° C. from 15° C. obtained by prior cooling with an ice bath. The mixture which solidified became fluid upon the addition of 37% aqueous formaldehyde (3.6 g., 0.04 mole), the temperature rose to 30° C. and carbon dioxide evolution began. The mixture was stirred an additional 12 hours, was taken up in ether and the organic phase separated and washed with water. The dried ether solution was stripped of solvent to leave a solid residue product, 3.7 g. of practically analytical purity.

Workup

  1. customrose to 25° C. from 15° C.
  2. customobtained
  3. temperatureby prior cooling with an ice bath
  4. customrose to 30° C.
  5. customthe organic phase separated
  6. washwashed with water
  7. customto leave a solid residue product, 3.7 g

Sources & evidence

ORD record
ord-bcafefd463434a369923d6a6c2a36c1a
Source dataset
uspto-grants-1981_03
Patent number
US04254131

Linked notes

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