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

HRID 330885Notes

Reaction equation

HRID 330885 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>[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

6

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 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.500 g (S)-5-dibenzylaminopiperidin-2-one are suspended in 15 ml of tetrahydrofuran. While cooling with the ice bath 0.175 g potassium-tert-butoxide are added. The reaction mixture is then stirred for 30 minutes at ambient temperature. While cooling with the ice bath 0.095 ml methyl iodide are added. The reaction mixture is then stirred for 48 hours at ambient temperature and then combined with a saturated NaCl solution. The product is extracted with ethyl acetate. 0.450 g of the product are obtained as an oil. Analytical HPLC-MS (method A): 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. extractionThe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-6c925f6d26154f2b9d3c1135a4a494f3
Source dataset
uspto-grants-2014_11
Patent number
US08877758B2

Reaction notes

Loading…