1-Methyl-4-(nitromethyl)piperidin-4-ol → 4-(Aminomethyl)-1-methylpiperidin-4-ol

HRID 44789Notes

Reaction equation

HRID 44789 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:9][N+:10]([O-])=O)([OH:8])[CH2:4][CH2:3]1>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:10][CH2:9][C:5]1([OH:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 2733771-Methyl-4-(nitromethyl)piperidin-4-ol

Product 1

HCID 64842624-(Aminomethyl)-1-methylpiperidin-4-olYield 106.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide (2.3 g of 20% on carbon) was added to a solution of 1-methyl-4-nitromethylpiperidin-4-ol (11.57 g) in ethanol (120 mL). The mixture was placed under hydrogen pressure (50 psi, 3.4×105 Pa) on a Parr apparatus for 55 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was rinsed with methanol (100 mL). The filtrate was concentrated under reduced pressure to provide 10.18 g of 4-aminomethyl-1-methylpiperidin-4-ol as a thick oil.

Workup

  1. customfor 55 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was rinsed with methanol (100 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4b5d7e18757e41bbb1458619541cc732
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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