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

HRID 1529504Notes

Reaction equation

HRID 1529504 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 mixed with a saturated NaCl solution. The product is extracted with ethyl acetate. 0.450g of the product are obtained as an oil.

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-ddef9d3eb1d54e2688f5a7b0abd9d12c
Source dataset
uspto-grants-2015_07
Patent number
US09090626B2

Reaction notes

Loading…