Hydrochloric Acid → (2S,3S)-2-phenylpiperidin-3-amine

HRID 2293708Notes

Reaction equation

HRID 2293708 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].O>CO.[Pt]>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27627843-Amino-2-phenylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 9812908(2S,3S)-2-phenylpiperidin-3-amineYield 87.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

In a bottle were placed 2.65 g (15.6 mmol) of 3-amino-2-phenylpyridine, 10.6 g of 5% platinum/carbon and 106 mL of 1.5 M HCl in methanol. The mixture was shaken under an atmosphere (ca. 40 p.s.i.) of hydrogen for 2.5 hours. Water was added to the system, the mixture was filtered through a pad of diatomaceous earth and the pad was rinsed with ca. 700 mL of water. The filtrate was made basic with solid sodium hydroxide and extracted with two portions of dichloromethane. The combined organic fractions were washed with water, dried (sodium sulfate) and concentrated with a rotary evaporator to obtain 2.4 g of the title compound as a yellow oil.

Workup

  1. filtrationthe mixture was filtered through a pad of diatomaceous earth
  2. washthe pad was rinsed with ca. 700 mL of water
  3. extractionextracted with two portions of dichloromethane
  4. washThe combined organic fractions were washed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-586596cf710c4a03b1a0ecba0ce21f4f
Source dataset
uspto-grants-1997_11
Patent number
US05686615

Reaction notes

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