Potassium Carbonate → HCID 12926620, compound

HRID 647515Notes

Reaction equation

HRID 647515 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([NH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]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]([Br:8])[N:3]=2)[CH2:21][CH2:20]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 14451564-Acetamidopiperidine

Product 1

HCID 12926620HCID 12926620, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.042 mole of 2,6-dibromopyridine, 0.056 mole of anhydrous potassium carbonate and 0.052 mole of 4-acetamidopiperidine in 75 ml of sulfolane is heated to 150° C. with stirring for 20 hours, then the sulfolane is concentrated to 1/5th of its volume, the reaction mixture is poured in 100 ml of water and extracted with diethyl ether (4×150 ml). The organic phase is washed with water, dried over anhydrous sodium sulfate, concentrated to dryness and the residue is crystallised in 40 ml of ethyl acetate. The 4-acetamido-1-(6-bromo-2-pyridyl)piperidine is thus obtained; m.p. 158° to 160° C.

Workup

  1. concentrationthe sulfolane is concentrated to 1/5th of its volume
  2. additionthe reaction mixture is poured in 100 ml of water
  3. extractionextracted with diethyl ether (4×150 ml)
  4. washThe organic phase is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customthe residue is crystallised in 40 ml of ethyl acetate

Sources & evidence

ORD record
ord-5766a322434d4c8fb18c972eb3b67dc1
Source dataset
uspto-grants-1983_10
Patent number
US04409228

Reaction notes

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