Formaldehyde → 1-Benzyl-3-dimethylaminopiperidine

HRID 1576384Notes

Reaction equation

HRID 1576384 reaction equation
[H][H].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][CH3:17])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:18]=O>[Pt]=O.C(O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]([CH3:18])[CH3:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 215125341-Benzyl-N-methylpiperidin-3-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 215125681-Benzyl-3-dimethylaminopiperidine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 0.30 g. of platinum oxide in 25 ml. of absolute ethanol was shaken under 35 psi of hydrogen for 1 hour. To this was added a solution of the 1-benzyl-3-methylaminopiperidine and 16 g. of 37 percent aqueous formaldehyde in 40 ml. of ethanol. The mixture was then shaken under ca. 50 psi of hydrogen until uptake ceased. Filtration and evaporation left an oil, which was dissolved in benzene and extracted with dilute hydrochloric acid. The extract was made strongly basic with sodium hydroxide and was extracted with methylene chloride. After drying, the solvent was evaporated, leaving 1-benzyl-3-dimethylaminopiperidine.

Workup

  1. additionA suspension of 0.30 g
  2. filtrationFiltration and evaporation
  3. waitleft an oil, which
  4. dissolutionwas dissolved in benzene
  5. extractionextracted with dilute hydrochloric acid
  6. extractionwas extracted with methylene chloride
  7. customAfter drying
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-27f52359274c4f4e93975ddff88d1d5e
Source dataset
uspto-grants-1976_09
Patent number
US03980788

Reaction notes

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