Water → HCID 12926611, compound

HRID 647508Notes

Reaction equation

HRID 647508 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]=[C:20]([O:24][CH3:25])[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]=[C:20]([O:24][CH3:25])[N:19]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 870092-Chloro-6-methoxypyridineHCID 14451564-Acetamidopiperidine

Product 1

HCID 12926611HCID 12926611, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.088 mole of 4-acetamidopiperidine, 15 g of potassium carbonate, 0.088 mole of 2-chloro-6-methoxypyridine in 100 ml of dimethylsulfoxide is heated with stirring to 130° C. for 50 hours, then it is cooled, the mixture is 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 on anhydrous sodium sulfate and evaporated to dryness. 4-acetamido-1-(6-methoxy-2-pyridyl)piperidine is thus obtained which, after crystallisation in 95% ethanol, melts at 125° to 127° C.

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 on anhydrous sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-af08170dc4604aaebb96c22421ea938b
Source dataset
uspto-grants-1983_10
Patent number
US04409228

Reaction notes

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