4-Methylpiperidine → 3-(3-(4-Methylpiperidino)-1,2,5-thiadiazol-4-yl)pyridine

HRID 1600280Notes

Reaction equation

HRID 1600280 reaction equation
Cl[C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][S:4][N:3]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C=O)C>[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[C:6]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[N:5][S:4][N:3]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole

Product 1

HCID 190753173-(3-(4-Methylpiperidino)-1,2,5-thiadiazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (10.80 g, 4 mmol) and 4-methylpiperidine (1.96 g, 20 mmol) in DMF (10 ml) was heated at 100° C. for 3 h. After evaporation water was added to the residue and extracted with ether. The combined and dried organic phases were evaporated and the residue purified by column chromatography (SiO2, eluent: ethyl acetate/methylene chloride (1:2)). Yield: 0.8 g (77%).

Workup

  1. customAfter evaporation water
  2. additionwas added to the residue
  3. extractionextracted with ether
  4. customdried organic phases were evaporated
  5. customthe residue purified by column chromatography (SiO2, eluent: ethyl acetate/methylene chloride (1:2))

Sources & evidence

ORD record
ord-46de92b72d9843ebb56fe4b466239373
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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