Sulfuric Acid → 1-Ethoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester

HRID 1962364

Reaction equation

HRID 1962364 reaction equation
S(=O)(=O)(O)[OH:2].[C:6]([C:8]1([NH:17][C:18](=[O:29])[CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[CH2:13][CH2:12][N:11]([O:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)#N.[C:30](=O)([O-])[O-:31].[Na+].[Na+]>CO>[CH3:30][O:31][C:6]([C:8]1([NH:17][C:18](=[O:29])[CH2:19][C:20]2[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])[CH2:13][CH2:12][N:11]([O:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 59614586N-(4-cyano-1-ethoxy-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide

Product 1

HCID 596145921-Ethoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.4 ml of concentrated sulfuric acid was slowly added to a solution of 4.3 g of N-(4-cyano-1-ethoxy-piperidin-4-yl)-2-(2,4,6-trimethyl-phenyl)-acetamide in 11 ml of methanol. After stirring 20 hours under reflux, the reaction mixture was allowed to cool down to room temperature and diluted with ice water. Sodium carbonate was added and the aqueous phase was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. Chromatography (dichloromethane+1% of ethanol) gave 3.2 g of 1-ethoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester as a solid, mp: 131-132° C.

Workup

  1. temperatureunder reflux
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b3f66b345844f11a12c2b3b771ed926
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Linked notes

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