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

HRID 1483792Notes

Reaction equation

HRID 1483792 reaction equation
[CH3:1][N+:2]([O-:4])=[O:3].CO[Na].[CH3:8][N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1>CCO>[CH3:8][N:9]1[CH2:14][CH2:13][C:12]([CH2:1][N+:2]([O-:4])=[O:3])([OH:15])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 740491-Methyl-4-piperidoneHCID 178418582HCID 178418582, compound

Product 1

HCID 2733771-Methyl-4-(nitromethyl)piperidin-4-olYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

CH3NO2 (6.6 mL, 122 mmol) and MeONa (221 mg, 4.1 mmol) was added to a solution of compound 1-methylpiperidin-4-one (10 mL, 81.3 mmol) in EtOH (10 mL). After 30 min more ethanol (15 mL) was added to facilitate stirring. The reaction mixture was stirred at room temperature for 2 days and then filtered through celite. The isolated solid was washed with ether to give the product 1-methyl-4-(nitromethyl)piperidin-4-ol (5.7 g, yield 40.4%). 1H-NMR (DMSO-d6/400 MHz): δ 5.01 (s, 1H), 4.47 (s, 2H), 2.41-2.40 (m, 2H), 2.21-2.15 (m, 2H), 2.12 (s, 3H), 1.64-1.53 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 days
  2. filtrationfiltered through celite
  3. washThe isolated solid was washed with ether

Sources & evidence

ORD record
ord-87000144ca504508be733c56ed76c994
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…