Sodium Chloride → (S)-5-dibenzylamino-1-methylpiperidin-2-one

HRID 1641336Notes

Reaction equation

HRID 1641336 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:9]1[CH2:14][NH:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23]C(C)([O-])C.[K+].CI.[Na+].[Cl-]>O1CCCC1.C(OCC)(=O)C>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]1[CH2:14][N:13]([CH3:23])[C:12](=[O:15])[CH2:11][CH2:10]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 10780155(S)-5-dibenzylaminopiperidin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 59708472(S)-5-dibenzylamino-1-methylpiperidin-2-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (S)-5-dibenzylamino-piperidin-2-one are suspended in 15 ml of tetrahydrofuran. While cooling with the ice bath 175 mg potassium-tert-butoxide are added. The reaction mixture is then stirred for 30 minutes at ambient temperature. While cooling with the ice bath 95 μl methyliodide are added. The reaction mixture is then stirred for 48 hours at ambient temperature and then combined with a saturated NaCl solution and ethyl acetate. The organic phase is dried and evaporated to dryness. 450 mg of the product are obtained as an oil. Analytical HPLC-MS (method D): RT=1.07 min.

Workup

  1. additionare added
  2. additionare added
  3. stirringThe reaction mixture is then stirred for 48 hours at ambient temperature
  4. customThe organic phase is dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-51f69d63b5c443aaa0880ed5aad65d67
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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