Formaldehyde → Piperidine, 1-methyl-4-phenyl-

HRID 271128Notes

Reaction equation

HRID 271128 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:15](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.O>[CH3:15][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 698734-PhenylpiperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 202391Piperidine, 1-methyl-4-phenyl-Yield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-phenylpiperidine (1.0 g, 6.2 mmol) was dissolved in THF (20 mL) and treated with formaldehyde (2.6 mL of a 37% solution in water). To the stirred reaction mixture was added sodium triacetoxyborohydride (2.63 g, 12.4 mmol). The reaction mixture was maintained at room temperature for 1 h, and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed with 5% aqueous NaHCO3 and brine, then dried over MgSO4. Evaporation of the solvent yielded 1-methyl-4-phenylpiperidine 113 (1.06 g, 97%) as a colorless oil.

Workup

  1. customTo the stirred reaction mixture
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with 5% aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c61288f661824cb48a816aabc07d3982
Source dataset
uspto-grants-2008_11
Patent number
US07452887B2

Reaction notes

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