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

HRID 647510Notes

Reaction equation

HRID 647510 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]([NH:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>S1(CCCC1)(=O)=O.[Cu]>[C:21]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH:27]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH2:26]1)(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21288N-Pyridin-4-ylacetamideHCID 8176622-Chloro-6-phenoxypyridine

Product 1

HCID 204851724-Acetamido-2-(6-phenoxy-2-pyridyl)piperidineYield 30%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.116 moles of 2-chloro-6-phenoxypyridine, 21.5 g of anhydrous potassium carbonate, 0.151 moles of 4-acetamidopyridine and 0.118 mole of copper in powder form in 100 ml of sulfolane is heated to 150° C. with stirring for 40 hours. The sulfolane is distilled, the residue is taken up with water, the suspension is treated with water and it is extracted with methylene chloride. The organic phase is washed with water, dried and concentrated to dryness. By crystallisation of the residue in diisopropylic ether, 4-acetamido-2-(6-phenoxy-2-pyridyl)piperidine is obtained; m.p. 104° to 106° C.

Workup

  1. distillationThe sulfolane is distilled
  2. additionthe suspension is treated with water and it
  3. extractionis extracted with methylene chloride
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customBy crystallisation of the residue in diisopropylic ether

Sources & evidence

ORD record
ord-5bf9257e65124006800c87f38633ee38
Source dataset
uspto-grants-1983_10
Patent number
US04409228

Reaction notes

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