Hydrochloric Acid → 2-Phenylpiperidin-3-amine

HRID 2304530Notes

Reaction equation

HRID 2304530 reaction equation
[NH2:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[H][H]>[Pt].O>[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27627843-Amino-2-phenylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 97940082-Phenylpiperidin-3-amine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

A 500 ml Parr bottle was charged with 5 grams of 5% platinum/carbon (50% water wet), 5 grams (0.0293 mol.) 3-amino-2-phenylpyridine (1 equivalent), 75 ml of water (15 vol.) and 25 ml of concentrated hydrochloric acid (5 vol.). The reaction was hydrogenated (maintaining the hydrogen pressure between 36 psi and 50 psi) until high pressure liquid chromatography (HPLC) indicated complete reaction. The catalyst was removed by filtration and the pH of the filtrate was adjusted from 0 to a stable 11.2 using 25% sodium hydroxide (NaOH). The aqueous layer was extracted twice with 50 ml of methylene chloride (CH2Cl2). The organic extracts were combined, dried with magnesium sulfate (MgSO4) and the filtrate was atmospherically distilled to an oil, 4.34 grams (84.1%).

Workup

  1. customreaction
  2. customThe catalyst was removed by filtration
  3. extractionThe aqueous layer was extracted twice with 50 ml of methylene chloride (CH2Cl2)
  4. dry with materialdried with magnesium sulfate (MgSO4)
  5. distillationthe filtrate was atmospherically distilled to an oil, 4.34 grams (84.1%)

Sources & evidence

ORD record
ord-e83416b75ac34e70b7facdde71557728
Source dataset
uspto-grants-2002_08
Patent number
US06436961B1

Reaction notes

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