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

HRID 257930Notes

Reaction equation

HRID 257930 reaction equation
Cl[C:2]1[C:3]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][S:5][N:6]=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:3]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[N:4][S:5][N:6]=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-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (10.80 g, 4 mmol) and 4-methylpiperidine (1.96 g, 20 mmol) in DMF (10 ml) was heated at lOOoC 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-01ddc961d1194f94b7138c5d8e559c36
Source dataset
uspto-grants-1993_11
Patent number
US05264444

Reaction notes

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