Potassium Carbonate → 4-[2-(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester

HRID 1962370Notes

Reaction equation

HRID 1962370 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].[CH:21]1([C:24]2[C:25]([CH3:35])=[CH:26][C:27]([CH3:34])=[C:28]([CH2:30][C:31](Cl)=[O:32])[CH:29]=2)[CH2:23][CH2:22]1>C(#N)C>[CH3:8][O:9][C:10]([C:12]1([NH:20][C:31](=[O:32])[CH2:30][C:28]2[CH:29]=[C:24]([CH:21]3[CH2:22][CH2:23]3)[C:25]([CH3:35])=[CH:26][C:27]=2[CH3:34])[CH2:17][CH2:16][N:15]([O:18][CH3:19])[CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59614607(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetyl chlorideHCID 666317834-Amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride

Product 1

HCID 596145774-[2-(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 4 g of potassium carbonate and 2.5 g of 4-amino-1-methoxy-piperidine-4-carboxylic acid methyl ester hydrochloride (preparation example P1, step P1.3) in 10 ml of acetonitrile was added at 0-5° C. a solution of 2.1 g of crude (5-cyclopropyl-2,4-dimethyl-phenyl)-acetyl chloride in 5 ml of acetonitrile. After stirring for 18 hours at room temperature, the solvent was removed in vacuo and the crude residue of 4-[2-(5-cyclopropyl-2,4-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester (3.2 g) was used without further purification in the next step.

Workup

  1. customwas added at 0-5° C.
  2. customthe solvent was removed in vacuo
  3. customthe crude residue of 4-[2-(5-cyclopropyl-2,4-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester (3.2 g) was used without further purification in the next step

Sources & evidence

ORD record
ord-8e60c3fea3394810878c76c30e556f8f
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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