Hydrochloric Acid → HCID 14965156, compound

HRID 1655404Notes

Reaction equation

HRID 1655404 reaction equation
CCN(CC)CC.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1.Cl.FC1C=CC(N2[C:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:28]=3[C:27]([CH2:35][OH:36])=N2)=CC=1>CCO>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:27]([CH2:35][OH:36])=[C:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C:29]3=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 69982(4-Fluorophenyl)hydrazineHCID 20094651HCID 20094651, compound

Product 1

HCID 14965156HCID 14965156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude diketone was dissolved in 60 mL of absolute EtOH and combined with 3.07 mL (22 mmol, 2.23 g) of Et3N and 3.45 g (21.1 mmol) of 4-fluorophenylhydrazine.HCl. The resulting solution was stirred under N2 overnight and refluxed for 4 h. A 30 mL portion of 1N aqueous HCl was added and the mixture was refluxed for an additional hour. The mixture was cooled and extracted with 200 mL of Et2O. The organic phase was washed with water, saturated aqueous NaHCO3, and brine and dried over Na2SO4. The solution was concentrated to give 5.50 g of a 1.2:1 mixture of 1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydrocycloheptapyrazole-3-methanol and the title compound as a brown oil. The crude product was crystallized from EtOAc:Et2O to afford 0.97 g (18%) of the title compound as an off-white solid, m.p. 177°-178° C.; 1H NMR (CDCl3, 300 MHz) 1.72 (m, 4), 1.85 (m, 2), 2.60 (m, 2), 2.80 (m, 2), 4.51 (d, 2, J=5 Hz), 7.15 (m, 2), 7.60 (m, 2); IR (KBr) 3240 (broad), 1513, 1223 cm-1 ; MS (DCI) m/z 261 (base). Anal. Calcd. for C15H17FN2O: C, 69.21; H, 6.58; N, 1076. Found C, 69.15; H, 6.77; N, 10.63.

Workup

  1. temperaturerefluxed for 4 h
  2. temperaturethe mixture was refluxed for an additional hour
  3. temperatureThe mixture was cooled
  4. extractionextracted with 200 mL of Et2O
  5. washThe organic phase was washed with water, saturated aqueous NaHCO3, and brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated
  8. customto give

Sources & evidence

ORD record
ord-74bd0cb022b945a9858f011eb7206f1f
Source dataset
uspto-grants-1993_10
Patent number
US05250561

Reaction notes

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