Water → HCID 12926612, compound

HRID 647509Notes

Reaction equation

HRID 647509 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CS(C)=O>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 79772-ChloropyridineHCID 11430Potassium CarbonateHCID 14451564-Acetamidopiperidine

Product 1

HCID 12926612HCID 12926612, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 12.5 g of 4-acetamidopiperidine, 15 g of potassium carbonate, 10 g of 2-chloropyridine in 100 ml of dimethylsulfoxide, is heated with stirring for 50 hours to 130° C., then it is cooled, poured into water and the suspension thus obtained is extracted with diethyl ether. The aqueous phase is extracted with methylene chloride, the organic phase is washed with water, it is dried over anhydrous sodium sulfate and evaporated to dryness. Thus, 4-acetamido-1-(2-pyridyl) piperidine is obtained which, after crystallisation in isopropanol and recrystallisation in ethyl acetate, melts at 165° to 168° C. Yield: 4.7 g (24.5% of the theoretical).

Workup

  1. temperatureis heated
  2. temperatureit is cooled
  3. customthe suspension thus obtained
  4. extractionis extracted with diethyl ether
  5. extractionThe aqueous phase is extracted with methylene chloride
  6. washthe organic phase is washed with water, it
  7. dry with materialis dried over anhydrous sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-38ffc030a5694aeab249c0e1997a3c7d
Source dataset
uspto-grants-1983_10
Patent number
US04409228

Reaction notes

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