Pyridine → HCID 68468494, compound

HRID 502990Notes

Reaction equation

HRID 502990 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:12]3[N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:15]4=[N:14][N:13]=3)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].N1C=CC=CC=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:23][S:24]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:12]3[N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:15]4=[N:14][N:13]=3)[CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:3][CH2:2]1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 68465905HCID 68465905, compound

Product 1

HCID 68468494HCID 68468494, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(1-Piperidin-4-ylcyclopentyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (302 mg) was dissolved in methylene chloride (5 ml) and then methanesulfonyl chloride (0.09 ml) and pyridine (0.24 ml) were added thereto, followed by stirring at room temperature for 6 hours. Furthermore, methanesulfonyl chloride (0.09 ml) and pyridine (0.57 ml) were added thereto, followed by stirring at room temperature for 16 hours. The reaction solution was diluted with a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform (10 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=1:9) and then the resulting solid washed with ethyl acetate to obtain 117 mg of 3-{1-[1-(methylsulfonyl)-4-piperidinyl]cyclopentyl}-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (white solid).

Workup

  1. stirringby stirring at room temperature for 16 hours
  2. extractionfollowed by extraction with chloroform (10 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography (methanol:chloroform=1:9)
  7. washthe resulting solid washed with ethyl acetate

Sources & evidence

ORD record
ord-b83ecc7bdd62418f8c0d7517885658b7
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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