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

HRID 474169
Notes
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Reaction equation

HRID 474169 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

Procedure

0.500 g (S)-5-dibenzylaminopiperidin-2-one are suspended in 15 ml of tetrahydrofuran. 0.175 g potassium-tert-butoxide are added while cooling with the ice bath. 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.

Workup

  1. additionare added
  2. stirringThe reaction mixture is then stirred for 48 hours at ambient temperature
  3. extractionThe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-49bc17cae1244acf831399cdd7e20b23
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637519B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes