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Potassium Carbonate → Methyl 4-[2-(2,5-dimethyl-phenyl)acetylamino]-1-methoxy-piperidine-4-carboxylate

HRID 1962359
Notes
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Reaction equation

HRID 1962359 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][O:9][C:10]([C:12]1([NH2:20])[CH2:17][CH2:16][N:15]([O:18][CH3:19])[CH2:14][CH2:13]1)=[O:11].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[CH2:29][C:30](Cl)=[O:31]>C(#N)C>[CH3:8][O:9][C:10]([C:12]1([NH:20][C:30](=[O:31])[CH2:29][C:23]2[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=2[CH3:21])[CH2:17][CH2:16][N:15]([O:18][CH3:19])[CH2:14][CH2:13]1)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22561615(2,5-Dimethylphenyl)acetyl chlorideHCID 666317834-Amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride

Product 1

HCID 44603928Methyl 4-[2-(2,5-dimethyl-phenyl)acetylamino]-1-methoxy-piperidine-4-carboxylateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Procedure

To 5.4 g of potassium carbonate and 2 g of 4-amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride in 10 ml of acetonitrile was added 1.94 g of (2,5-dimethyl-phenyl)-acetyl chloride in 5 ml of acetonitrile at a temperature of 0-5° C. After stirring for 22 hours at room temperature, the reaction mixture was poured on ice water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to yield 2.13 g of 4-[2-(2,5-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester as a beige crystalline solid, mp: 91-93° C.

Workup

  1. additionthe reaction mixture was poured on ice water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3c2ea11033544c69902a492fd2faad82
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415369B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes