Dichloromethane → (2S,3S)-2-phenylpiperidin-3-amine

HRID 2304531Notes

Reaction equation

HRID 2304531 reaction equation
C(O)(=O)C(C1C=CC=CC=1)O.[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.C(Cl)Cl.[OH-].[Na+]>O>[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

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 70160941HCID 70160941, compound

Product 1

HCID 9812908(2S,3S)-2-phenylpiperidin-3-amineYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A magnetically stirred 1L erlenmeyer flask was charged with 20 grams (0.06 mol.) of the (+)-(2S,3S)-3-amino-2-phenylpiperidine mandelate salt (1 equivalent), 200 ml CH2Cl2 (10 vol.) and 200 ml of water (10 vol.). The pH of this slurry was adjusted from 5.1 to a stable 12 with 25% NaOH. The layers were separated and the aqueous layer was extracted once with 200 ml of CH2Cl2. The combined organic extracts were treated with 1 gram (5% by wt.) of Darco® G-60 for 15 minutes then dried with MgSO4 for 30 minutes. The Darco® and MgSO4 were removed by filtration and the filtrate was concentrated atmospherically to yield 7.36 grams of the title compound. Oil, 67.8% yield.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once with 200 ml of CH2Cl2
  3. additionThe combined organic extracts were treated with 1 gram (5% by wt.) of Darco® G-60 for 15 minutes
  4. dry with materialthen dried with MgSO4 for 30 minutes
  5. customThe Darco® and MgSO4 were removed by filtration
  6. concentrationthe filtrate was concentrated atmospherically

Sources & evidence

ORD record
ord-56a31470429e490d95e8eb081461fb96
Source dataset
uspto-grants-2002_08
Patent number
US06436961B1

Reaction notes

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