Carbon Dioxide → 2-[(4-Hydroxy-4-phenyl-1-piperidyl)methyl]propenenitrile

HRID 126841Notes

Reaction equation

HRID 126841 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[OH:7][C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C=O.[C:22](=O)=O>O1CCOCC1>[OH:7][C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][N:11]([CH2:22][C:3](=[CH2:4])[C:1]#[N:2])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 130410372-[(4-Hydroxy-4-phenyl-1-piperidyl)methyl]propenenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of cyanoacetic acid (4.3 g., 0.05 mole) in 15 ml. of dioxane was cooled with an ice bath, and 4-hydroxy-4-phenylpiperidine (8.8 g., 0.05 mole) added while maintaining an internal temperature of 20°-25° C. Upon complete addition and a further fifteen minutes of stirring 37% aqueous formaldehyde (9 gm., 0.10 mole) was added dropwise in approximately five minutes. When approximately half was added carbon dioxide evolution was observed, the maximum internal temperature was 28° C. The reaction mixture was stirred overnight, mixed with 100 ml. of methylene chloride, the organic phase separated washed with water and salt solution. Upon removal of solvent the product was obtained as an oil, 10.5 g., in practically analytical purity.

Workup

  1. temperaturewhile maintaining an internal temperature of 20°-25° C
  2. additionUpon complete addition
  3. additionwas added dropwise in approximately five minutes
  4. customwas 28° C
  5. additionmixed with 100 ml
  6. customof methylene chloride, the organic phase separated
  7. washwashed with water and salt solution
  8. customUpon removal of solvent the product
  9. customwas obtained as an oil, 10.5 g

Sources & evidence

ORD record
ord-2b2a6e5ae4814ff9a5a1ea69add86605
Source dataset
uspto-grants-1981_03
Patent number
US04254131

Reaction notes

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