Hydrochloric Acid → 2,5-Dimethyl-4-(piperidin-3-yl)aniline

HRID 536349Notes

Reaction equation

HRID 536349 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:6]([CH3:15])=[CH:5][C:3]=1[NH2:4].Cl>CO.O=[Pt]=O>[CH3:1][C:2]1[CH:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[C:6]([CH3:15])=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 582571172,5-Dimethyl-4-(pyridin-3-yl)aniline

Product 1

HCID 671555442,5-Dimethyl-4-(piperidin-3-yl)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

2,5-Dimethyl-4-(pyridin-3-yl)aniline (403 mg, 2.03 mmol) was dissolved in MeOH (5 mL) and conc. aqueous HCl (1 mL), followed by addition of PtO2 (40 mg). The flask was purged with H2 and the reaction was vigorously stirred at rt under H2 (1 atm). After two days, LCMS shows the completion of the reaction. The catalyst was removed by filtration and the remaining solution was concentrated in vacuo to give 2,5-Dimethyl-4-(piperidin-3-yl)aniline as a white solid, which can be used in subsequent reactions without further purification; ESMS m/z 205.2 (M+H+).

Workup

  1. customThe flask was purged with H2
  2. customthe completion of the reaction
  3. customThe catalyst was removed by filtration
  4. concentrationthe remaining solution was concentrated in vacuo

Sources & evidence

ORD record
ord-0324a235dc46422f9abcf4eee6ffc291
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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