Potassium Carbonate → 4-Acetamido-1-(6-methyl-2-pyridyl)piperidine

HRID 647512Notes

Reaction equation

HRID 647512 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)(=[O:17])[CH3:16]>S1(CCCC1)(=O)=O>[C:15]([NH:18][CH:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=2)[CH2:21][CH2:20]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21288N-Pyridin-4-ylacetamideHCID 876016-Chloro-2-picoline

Product 1

HCID 129266184-Acetamido-1-(6-methyl-2-pyridyl)piperidineYield 28%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

0.042 mole of 2-chloro-6-methylpyridine, 0.056 mole of anhydrous potassium carbonate and 0.052 mole of 4-acetamidopyridine in 75 ml of sulfolane are heated to 150° C. with stirring for 24 hours, then the sulfolane is concentrated up to 1.5 of its volume, the mixture is poured into 100 ml of water and extraction is effected four times with 150 ml of diethyl ether. The organic phase is washed with water, it is dried over anhydrous sodium sulfate, concentrated to dryness and the residue is crystallised in 40 m of ethyl acetate. Thus, the 4-acetamido-1-(6-methyl-2-pyridyl)piperidine is obtained; m.p. 145° to 147° C.

Workup

  1. concentrationthe sulfolane is concentrated up to 1.5 of its volume
  2. additionthe mixture is poured into 100 ml of water and extraction
  3. washThe organic phase is washed with water, it
  4. dry with materialis dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customthe residue is crystallised in 40 m of ethyl acetate

Sources & evidence

ORD record
ord-a522ec499de54b678a31a66f02df464a
Source dataset
uspto-grants-1983_10
Patent number
US04409228

Reaction notes

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