3,5-Dimethylpiperidine → HCID 58792110, compound

HRID 2222135Notes

Reaction equation

HRID 2222135 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[CH3:9][CH:10]1[CH2:15][CH:14]([CH3:16])[CH2:13][NH:12][CH2:11]1>CN(C)C=O.COC(C)(C)C>[CH3:8][S:7][C:4]1[N:3]=[C:2]([N:12]2[CH2:13][CH:14]([CH3:16])[CH2:15][CH:10]([CH3:9])[CH2:11]2)[S:6][N:5]=1

Participants

5

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 58792110HCID 58792110, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

In 9 ml of N,N-dimethylformamide was dissolved 740 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole, and 1.25 g of 3,5-dimethylpiperidine (a mixture of 8:2 geometrical isomers) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 20 minutes. The reaction mixture was diluted with tert-butyl methyl ether, and extracted with tert-butyl methyl ether after the addition of 10% hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 860 mg of 3-methylthio-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole.

Workup

  1. additiona mixture of 8:2 geometrical isomers)
  2. additionwas added dropwise under ice-
  3. temperaturecooling
  4. extractionextracted with tert-butyl methyl ether
  5. additionafter the addition of 10% hydrochloric acid
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0be2c8dfbad412186455aaf7077029d
Source dataset
uspto-grants-2008_05
Patent number
US07371746B2

Reaction notes

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