Hydrazine hydrate (1:1) → HCID 178479848, compound

HRID 2254102Notes

Reaction equation

HRID 2254102 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH:10]1[CH2:16][CH:15]2[N:17]([CH3:18])[CH:12]([CH2:13][CH2:14]2)[CH2:11]1)=O.O.[NH2:20][NH2:21]>C(O)C>[NH:20]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]([CH:10]2[CH2:16][CH:15]3[N:17]([CH3:18])[CH:12]([CH2:13][CH2:14]3)[CH2:11]2)=[N:21]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9837778HCID 9837778, compound

Product 1

HCID 178479848HCID 178479848, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2-fluorophenyl)(8-methyl-8-azabicyclo-[3.2.1]octan-3-yl) methanone (24.6 g), hydrazine hydrate (14.4 ml), and ethanol (250 ml) was heated to reflux for four hours. The reaction was cooled to room temperature and concentrated to an oil. This residue was dissolved in dimethylformamide (DMF) (250 ml). Potassium carbonate (28 g) was added to the mixture which was subsequently heated at reflux for 2 days. The reaction mixture was cooled and filtered and the DMF was removed in vacuo. The residue was dissolved in ethanol and 5.2 g of 3-(1H-indazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane precipitated from solution, as a powder, m.p. 191°-192° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for four hours
  3. concentrationconcentrated to an oil
  4. dissolutionThis residue was dissolved in dimethylformamide (DMF) (250 ml)
  5. additionPotassium carbonate (28 g) was added to the mixture which
  6. temperaturewas subsequently heated
  7. temperatureat reflux for 2 days
  8. temperatureThe reaction mixture was cooled
  9. filtrationfiltered
  10. customthe DMF was removed in vacuo
  11. dissolutionThe residue was dissolved in ethanol
  12. custom5.2 g of 3-(1H-indazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane precipitated from solution, as a powder, m.p. 191°-192° C.

Sources & evidence

ORD record
ord-346e092a91eb4086832ac0c005773aa9
Source dataset
uspto-grants-1993_08
Patent number
US05234931

Reaction notes

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