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

HRID 863584

Reaction equation

HRID 863584 reaction equation
CO.C(O)C.Cl.COC1C=CC=CC=1C[NH:12][C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][C@H:14]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.[C].[Pd]>[NH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][C@H:14]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 887MethanolHCID 5311057CP-99994

Product 1

HCID 9812908(2S,3S)-2-phenylpiperidin-3-amine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

In a bottle were placed 9 g of 10% palladium-carbon, 180 ml of methanol, 275 ml of ethanol, 6.5 ml of concentrated hydrochloric acid and 9 g of the hydrochloride salt of (2S,3S)-3-(2-methoxybenzylamino)-2-phenylpiperidine. The mixture was shaken under hydrogen (40 p.s.i.) overnight, after which 9 g of additional catalyst were added to the system and the mixture was shaken under hydrogen for 1 day. The mixture was diluted with water (250 mL), filtered through diatomaceous earth (Celite (trademark)) and the Celite was rinsed well with water. The filtrate was concentrated to a volume of ca. 600-700 mL, made basic with concentrated aqueous sodium hydroxide and extracted with chloroform. The chloroform extracts were dried (sodium sulfate) and concentrated to obtain 4.4 g of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was shaken under hydrogen for 1 day
  2. filtrationfiltered through diatomaceous earth (Celite (trademark))
  3. washthe Celite was rinsed well with water
  4. concentrationThe filtrate was concentrated to a volume of ca. 600-700 mL
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform extracts were dried (sodium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e32cb3f0ef0e44669df25f7b69588d8d
Source dataset
uspto-grants-1998_02
Patent number
US05721255

Linked notes

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