Piperidine → HCID 50997322, compound

HRID 1399717Notes

Reaction equation

HRID 1399717 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][C:6]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 86665653Methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

Product 1

HCID 50997322HCID 50997322, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.081 g; 0.25 mmol), piperidine (0.122 mL; 1.228 mmol) and potassium carbonate (0.102 mg; 0.737 mmol) in acetonitrile (1 mL) was irradiated at 130° C. for 2 h in a microwave oven. The mixture was partitioned between brine and ethyl acetate, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane furnished 0.042 g (46%) of the title compound as a colorless oil.

Workup

  1. customwas irradiated at 130° C. for 2 h in a microwave oven
  2. customThe mixture was partitioned between brine and ethyl acetate
  3. customthe phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane

Sources & evidence

ORD record
ord-f058bba8183e46d68e4d6e4f8de43957
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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