Formaldehyde → 2-[(4-Cyclohexylmethyl-1-piperidyl)methyl]propenenitrile

HRID 66662Notes

Reaction equation

HRID 66662 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].O1CCOC[CH2:8]1.[CH:13]1([CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C=O>O>[CH:13]1([CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([CH2:8][C:3](=[CH2:4])[C:1]#[N:2])[CH2:24][CH2:25]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 312751,4-DioxaneHCID 988834-(Cyclohexylmethyl)piperidine

Product 1

HCID 130410362-[(4-Cyclohexylmethyl-1-piperidyl)methyl]propenenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyanoacetic acid (0.9 g., 0.01 mole) was dissolved in 6 ml. of dioxane and 1 ml. of water. In a 15 minute period, 4-cyclohexylmethylpiperidine (1.8 g., 0.01 mole) was added. After an additional 15 minutes, 37% aqueous formaldehyde (1.8 g., 0.02 mole) was dripped in over a two minute period. The reaction mixture was agitated twelve hours at 20°-25° C., extracted with 200 ml. of ether, water washed, dried over anhydrous sodium sulfate, filtered and stripped. A yield of 1.2 g. of high purity product was obtained as a residue.

Workup

  1. customwas dripped in over a two minute period
  2. extractionextracted with 200 ml
  3. washof ether, water washed
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customof high purity product was obtained as a residue

Sources & evidence

ORD record
ord-49f41e3c9fd34342a345cc8ae596aa63
Source dataset
uspto-grants-1982_08
Patent number
US04342873

Reaction notes

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