Carbon Dioxide → 2-Methylpiperidine

HRID 66651

Reaction equation

HRID 66651 reaction equation
C(CC(O)=O)#N.[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(=O)=O.[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1CC(=C)C#N>CCOCC.C(Cl)Cl.C(O)C.O1CCOCC1>[C:7]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8].[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]1

Participants

11

Reactant 5

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 74661Piperidine, 4-(1,1-dimethylethyl)-HCID 542209882-[(2-Methyl-1-piperidyl)methyl]propenenitrile

Product 2

HCID 79742-MethylpiperidineHCID 74661Piperidine, 4-(1,1-dimethylethyl)-

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 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. In place of 4-t-butylpiperidine, the use of 2-methylpiperidine (0.02 mole) provided 2-[(2-methyl-1-piperidyl)methyl]propenenitrile as a colorless oil, RfSiO2 0.58 (5% ethanol in methylene chloride).

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-b90ebba6148c4c49a5ca4747826d7ecb
Source dataset
uspto-grants-1982_08
Patent number
US04342872

Linked notes

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