Nitromethane → 4-Hydroxy-4-nitromethyl-1-(4-pyridyl)piperidine

HRID 25042Notes

Reaction equation

HRID 25042 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[Na].[N:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1>CO>[OH:18][C:15]1([CH2:4][N+:1]([O-:3])=[O:2])[CH2:14][CH2:13][N:12]([C:9]2[CH:8]=[CH:7][N:6]=[CH:11][CH:10]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 5360545SodiumHCID 113327931-(Pyridin-4-yl)piperidin-4-one

Product 1

HCID 219225514-Hydroxy-4-nitromethyl-1-(4-pyridyl)piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of nitromethane (2.31 ml) in methanol (5.4 ml) was added sodium (70 mg) at ice-cooled temperature. The resulting mixture was added dropwise to a solution of 1-(4-pyridyl)-4-piperidone (5.36 g) in methanol (10.7 ml) at ice-cooled temperature for 10 minutes, and stirred for 15 hours at room temperature. The precipitate was filtered, and washed with methanol to obtain the title compound (5.31 g).

Workup

  1. temperaturecooled temperature
  2. temperaturecooled temperature for 10 minutes
  3. filtrationThe precipitate was filtered
  4. washwashed with methanol

Sources & evidence

ORD record
ord-7855da9b504f4967aa5a6cb749065d82
Source dataset
uspto-grants-2005_02
Patent number
US06858599B2

Reaction notes

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