Piperidine → Benzonitrile, 3-[6-(1-piperidinyl)-1,2,4-triazolo[4,3-b]pyridazin-3-yl]-

HRID 346500Notes

Reaction equation

HRID 346500 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[N:9][N:10]=2)[N:7]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[N:19]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=4)[C:14]#[N:15])=[N:9][N:10]=3)[N:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 23057961HCID 23057961, compound

Product 1

HCID 10286348Benzonitrile, 3-[6-(1-piperidinyl)-1,2,4-triazolo[4,3-b]pyridazin-3-yl]-

Procedure

A mixture of 3-(6-chloro-1,2,4-triazolo[4,3-b]pyridazin-3-yl)benzonitrile (450 mg) and piperidine (5 ml) was stirred with heating under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and the resultant residue was extracted with chloroform. The extract was washed with saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant crude crystals were recrystallized from ethanol to obtain 3-[6-(piperidin-1-yl)-1,2,4-triazolo[4,3-b]pyridazin-3-yl)benzonitrile (435 mg) as slightly yellowish crystals.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. extractionthe resultant residue was extracted with chloroform
  5. washThe extract was washed with saturated aqueous solution of ammonium chloride and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-1556dc0b495942b29f520965814a2579
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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