Hydrochloric Acid → HCID 15229928, compound

HRID 1655402Notes

Reaction equation

HRID 1655402 reaction equation
CCN(CC)CC.[C:8]([O:11][CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O)=O)(=[O:10])[CH3:9].[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1.Cl>CCO>[C:8]([O:11][CH2:12][C:13]1[N:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[N:30]=[C:16]2[C:15]=1[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69982(4-Fluorophenyl)hydrazineHCID 12326206HCID 12326206, compound

Product 1

HCID 15229928HCID 15229928, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Et3N (0.717 mL, 0.520 g, 5.14 mmol) was added to a stirring suspension of 1.00 g (5.04 mmol) of 2-acetoxyacetylcyclohexanone (Dolmazon, R.; Gelin, S. J. Heterocyclic Chem., 1982, 19, 117-121) and 0.820 g (5.04 mmol) of 4-fluorophenylhydrazine.HCl in 20 mL of absolute EtOH. The resulting solution was stirred under N2 for 4 h at room temperature and refluxed for 6 h. The mixture was concentrated and the residue was partitioned between 100 mL of Et2O and 50 mL of dilute aqueous HCl. The Et2O layer was washed with water, saturated aqueous NaHCO3, and brine. After drying over Na2SO4, the solution was concentrated to give 1.43 g of light brown solid. Recrystallization from EtOAc:hexanes afforded 0.753 g (52%) of the title compound as a white solid, m.p. 128.5°-129.5° C.; 1H NMR (CDCl3, 400 MHz) 1.85 (m, 4), 2.07 (s, 3), 2.60 (t, 2, J=6 Hz), 2.73 (t, 2, J=6 Hz), 5.00 (s, 2), 7.15 (t, 2, J=9 Hz), 7.45 (dd, 2, J=5, 9 Hz); IR (KBr) 1740, 1220 cm-1 ; MS (DCI) m/z 289 (base), 228 . Anal. Calcd. for C16H17FN2O2 : C, 66.65; H, 5.94; N, 9.72. Found: C, 66.74; H, 5.89; N, 9.61.

Workup

  1. temperaturerefluxed for 6 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between 100 mL of Et2O and 50 mL of dilute aqueous HCl
  4. washThe Et2O layer was washed with water, saturated aqueous NaHCO3, and brine
  5. dry with materialAfter drying over Na2SO4
  6. concentrationthe solution was concentrated
  7. customto give 1.43 g of light brown solid
  8. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-2ce8a37aa538435882a7435e05c95d32
Source dataset
uspto-grants-1993_10
Patent number
US05250561

Reaction notes

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