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

HRID 2293709Notes

Reaction equation

HRID 2293709 reaction equation
O.CO.Cl.COC1C=CC=CC=1C[NH:10][C@H:11]1[CH2:16][CH2:15][CH2:14][NH:13][C@H:12]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[C].[Pd].C(O)C>[NH2:10][C@H:11]1[CH2:16][CH2:15][CH2:14][NH:13][C@H:12]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 5311057CP-99994

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In a bottle were placed 31 g of 10% palladium-carbon, 50 mL of water, 300 mL of methanol, 450 mL of ethanol, 20 mL of concentrated aqueous hydrochloric acid and 15 g (0.04 mole) of the hydrochloride salt of (2S,3S)-3-(2-methoxybenzyl)amino-2-phenylpiperdine. The mixture was shaken under hydrogen (40 p.s.i.) for 1 day and filtered through a pad of diatomaceous earth. The pad was rinsed with 2N aqueous hydrochloric acid (HCl), water, ethanol and water and concentrated with a rotary evaporator. Water was added to the residue and the mixture was made basic using 4N aqueous sodium hydroxide (NaOH). The mixture was extracted with four portions of dichloromethane, and the extracts were dried over magnesium sulfate (MgSO4) and concentrated to obtain 2.23 g of the title compound. The aqueous fraction was concentrated to dryness and triturated with chloroform. Concentration of the chloroform solution afforded an additional 4.15 g of title compound. The product obtained in this manner had spectral properties identical to those of the product of Example 1.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. washThe pad was rinsed with 2N aqueous hydrochloric acid (HCl), water, ethanol and water
  3. concentrationconcentrated with a rotary evaporator
  4. additionWater was added to the residue
  5. extractionThe mixture was extracted with four portions of dichloromethane
  6. dry with materialthe extracts were dried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cff8a06ed12c4406ac47c1a58ab3d408
Source dataset
uspto-grants-1997_11
Patent number
US05686615

Reaction notes

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