HCID 43461694, compound → HCID 43373464, compound

HRID 1716888Notes

Reaction equation

HRID 1716888 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)[CH2:4][CH2:3]1>[Pd].CO>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 43461694HCID 43461694, compound

Product 1

HCID 43373464HCID 43373464, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Alternatively, charge a 2 L Parr bottle with 1-methyl-4-(3-nitrophenylamino)piperidine (100 g; 0.425 mol), 10% Pd/C (5 g) and methanol (1 L). Shake the mixture overnight under an initial hydrogen pressure of 4 atm, keeping the temperature below 35° C. Filter off the catalyst and wash with methanol (100 mL). Concentrate the filtrates under reduced pressure to provide 1-methyl-4-(3-aminophenylamino)piperidine as a red oil (95.7 g, 100% yield) which crystallizes upon standing at room temperature.

Workup

  1. customthe mixture overnight
  2. customthe temperature below 35° C
  3. filtrationFilter off the catalyst
  4. washwash with methanol (100 mL)
  5. concentrationConcentrate the filtrates under reduced pressure

Sources & evidence

ORD record
ord-91b0f056042d4e5796b2c1667fac6918
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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