6-(4,4-Ethylenedioxy-1-piperidinyl)-8-methyl-1,2,4-triazolo [4,3-b]pyridazine → 1-(8-Methyl-1,2,4-triazolo [4,3-b]pyridazin-6-yl)-4-piperidinone

HRID 1492398Notes

Reaction equation

HRID 1492398 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:10]=[C:11]([CH3:18])[C:12]4[N:13]([CH:15]=[N:16][N:17]=4)[N:14]=3)[CH2:5][CH2:4]2)[O:2]1>C(O)(=O)C>[CH3:18][C:11]1[C:12]2[N:13]([CH:15]=[N:16][N:17]=2)[N:14]=[C:9]([N:6]2[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]2)[CH:10]=1

Participants

3

Reactant 1

HCID 232003096-(4,4-Ethylenedioxy-1-piperidinyl)-8-methyl-1,2,4-triazolo [4,3-b]pyridazine

Product 1

HCID 189505491-(8-Methyl-1,2,4-triazolo [4,3-b]pyridazin-6-yl)-4-piperidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 62.5 g of 6-(4,4-ethylenedioxy-1-piperidinyl)-8-methyl-1,2,4-triazolo [4,3-b]pyridazine in 350 ml of aqueous 10% acetic acid was refluxed for 7 hours. The solvent was then evaporated under reduced pressure and the residue was taken up in 1100 ml of boiling ethanol. The ethanol solution was concentrated to 600 ml and cooled in an ice bath. The crystalline solid which formed was separated by filtration, washed with fresh ethanol and then with ethyl ether and dried to give 1-(8-methyl-1,2,4-triazolo [4,3-b]pyridazin-6-yl)-4-piperidinone as cream-colored needles melting at about 196.5°-199° C.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. concentrationThe ethanol solution was concentrated to 600 ml
  3. temperaturecooled in an ice bath
  4. customThe crystalline solid which formed
  5. customwas separated by filtration
  6. washwashed with fresh ethanol
  7. dry with materialwith ethyl ether and dried

Sources & evidence

ORD record
ord-63c8a031fbde412ebb1d824d5e552662
Source dataset
uspto-grants-1994_12
Patent number
US05374632

Reaction notes

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