Sodium Hydroxide → HCID 18950551, compound

HRID 1492400Notes

Reaction equation

HRID 1492400 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([CH3:20])[C:14]3[N:15]([CH:17]=[N:18][N:19]=3)[N:16]=2)[CH2:7][CH:6]1[Se:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:20][C:13]1[C:14]2[N:15]([CH:17]=[N:18][N:19]=2)[N:16]=[C:11]([N:8]2[CH2:9][CH2:10][CH:5]([OH:4])[CH:6]([Se:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:7]2)[CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18950545HCID 18950545, compound

Product 1

HCID 18950551HCID 18950551, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.6 g of 4-acetoxy-1-(8-methyl-1,2,4-triazolo [4,3-b]pyridazin-6-yl)-3-(phenylselenyl)piperidine in 25 ml of ethanol was stirred at room temperature while 10 ml of 1N sodium hydroxide was added. After stirring an additional 30 minutes at room temperature, the reaction was partitioned in water/dichloromethane. The layers were separated, the aqueous phase was washed with fresh dichloromethane and the combined organic layers were dried over anhydrous sodium sulfate and evaporated to give a colorless glass. When this material was boiled in 50 ml of ethyl acetate, a crystalline material formed. After cooling to room temperature, the product was collected and dried to give 1-(8-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-3-(phenylselenyl)-4-piperidinol melting at about 157°-160° C.

Workup

  1. additionwas added
  2. customthe reaction was partitioned in water/dichloromethane
  3. customThe layers were separated
  4. washthe aqueous phase was washed with fresh dichloromethane
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. customevaporated
  7. customto give a colorless glass
  8. customa crystalline material formed
  9. temperatureAfter cooling to room temperature
  10. customthe product was collected
  11. customdried

Sources & evidence

ORD record
ord-35724dc22bc34dbaa8e966bec6126753
Source dataset
uspto-grants-1994_12
Patent number
US05374632

Reaction notes

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