Hydrazine hydrate (1:1) → HCID 178479849, compound

HRID 1742738Notes

Reaction equation

HRID 1742738 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)=O.O.[NH2:21][NH2:22]>C(O)C>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9]([CH:11]3[CH2:17][CH:16]4[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]4)[CH2:12]3)=[N:21][NH:22]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19007838HCID 19007838, compound

Product 1

HCID 178479849HCID 178479849, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2,4-difluorophenyl)(8-methyl-8-azabicyclo-[3.2.1]octan-3-yl)methanone (25.5 g), hydrazine hydrate (21 g) and ethanol (250 ml) was heated at reflux for 16 hours. The reaction mixture was concentrated to an oil on the rotary evaporator. The residue was dissolved in DMF (350 ml) and potassium carbonate (25 g) was added to the mixture which was refluxed for 16 hours. The mixture was cooled, filtered and stripped down in vacuo. The residue was dissolved in hot ethanol to yield 4.96 g of a solid. Recrystallization from ethanol gave 3.88 g of crystals, m.p. 235°-236° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated to an oil on the rotary evaporator
  4. dissolutionThe residue was dissolved in DMF (350 ml)
  5. additionpotassium carbonate (25 g) was added to the mixture which
  6. temperaturewas refluxed for 16 hours
  7. temperatureThe mixture was cooled
  8. filtrationfiltered
  9. dissolutionThe residue was dissolved in hot ethanol

Sources & evidence

ORD record
ord-400fb8cd81d24eff95d89d02117407b0
Source dataset
uspto-grants-1994_08
Patent number
US05340936

Reaction notes

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