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

HRID 1022371Notes

Reaction equation

HRID 1022371 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].O>C(#N)C>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[CH2:29][C:30]([NH:20][C:12]1([C:10]([O:9][CH3:8])=[O:11])[CH2:17][CH2:16][N:15]([O:18][CH3:19])[CH2:14][CH2:13]1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 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 6342AcetonitrileSolvent2×

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, 1.94 g of (2,5-dimethyl-phenyl)-acetyl chloride in 5 ml of acetonitrile are added at a temperature of 0-5° C. After stirring for 22 h at room temperature the reaction mixture is poored on cold water and extracted with ethyl-acetate. The organic phase is dried over sodium sulfate, filtered and evaporated to yield 2.13 g of methyl 4-[2-(2,5-dimethyl-phenyl)acetylamino]-1-methoxy-piperidine-4-carboxylate as beige cristalline solid. 1H-NMR (CDCl3): □ 1.95-2.30 (br signals, total 4H), 2.27 (s, 3H), 2.33 (s, 3H), 2.77-3.23 (br signals, total 4H), 3.48 (s, 3H), 3.54 (s, 2H), 3.71 (s, 3H), 5.40 (br s, 1H), 7.02 (s, 1H), 7.04 (d, 1H), 7.11 (d, 1H).

Workup

  1. extractionextracted with ethyl-acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d46bdca5a38944a494ab77b3a802f691
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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