Nitromethane → 1-Methyl-4-(nitromethyl)piperidin-4-ol

HRID 44788

Reaction equation

HRID 44788 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[CH3:5][N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1>C(O)C.C[O-].[Na+]>[CH3:5][N:6]1[CH2:11][CH2:10][C:9]([CH2:4][N+:1]([O-:3])=[O:2])([OH:12])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 6375NitromethaneHCID 740491-Methyl-4-piperidone

Product 1

HCID 2733771-Methyl-4-(nitromethyl)piperidin-4-olYield 73.4%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 702EthanolSolvent2×

Procedure

Nitromethane (6.6 mL, 122.0 mmol) and sodium methoxide (0.94 mL of 25 wt % in methanol, 4.1 mmol) were added to a solution of 1-methyl-4-piperidone (10 mL, 81.3 mmol) in ethanol (10 mL). After 30 minutes more ethanol (15 mL) was added to facilitate stirring. The reaction mixture was stirred at ambient temperature for 2 days and then filtered. The isolated solid was rinsed with ether to provide 10.39 g of 1-methyl-4-nitromethylpiperidin-4-ol as a white powder. An additional 1.18 g was isolated from the filtrate.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 days
  2. filtrationfiltered
  3. washThe isolated solid was rinsed with ether

Sources & evidence

ORD record
ord-171affc250c54ee99467abab81fe1169
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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