HCID 12815016, compound → HCID 14371249, compound

HRID 1164920Notes

Reaction equation

HRID 1164920 reaction equation
O=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([CH2:9][C:10]([OH:12])=[O:11])[CH2:3]1.Cl.[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][N:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)N)=[CH:17][CH:16]=1>C(O)(C)(C)C>[F:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:20]([CH2:19][C:18]1[CH:29]=[CH:30][C:15]([Cl:14])=[CH:16][CH:17]=1)[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([CH2:9][C:10]([OH:12])=[O:11])[C:3]2=1

Participants

4

Reactant 2

HCID 12815016HCID 12815016, compoundHCID 145912421-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride

Product 1

HCID 14371249HCID 14371249, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 1.10 g of 3-oxo-cycloheptaneacetic acid in 35 mL tert-butanol was added 2.13 g of 1-(p-chlorobenzyl)-1-(p-fluorophenyl) hydrazine hydrochloride, The reaction mixture was refluxed under nitrogen for 18 h, cooled to room temperature and then evaporated to dryness. The resultant residue was partitioned between water and ethyl acetate. The organic layer was washed with 1N HCl (2X), water (2X) and brine and dried over MgSO4. Filtration and concentration gave oil which was purified by flash chromatography on silica gel. Elution of the column with a mixture of hexane-ethyl acetate (7:3) gave the title compound substituted at the 10-position, mp 138°-139° C. IR (KBr) 1703 cm-1. 'H NMR (CDCl3, 250 MHz) w 1.32-1.54 (m, 1H),2.60-2.87 (m, 2H), 2.65 (d, J=7.5 Hz, 2H), 3.72-3.83 (m, 1H), 5.25 (s, 2H), 6.78-6.88 (m, 1H), 6.81 (d, J=8.0 Hz, 2H), 7.04 (d,d, J=4.5, 9.0 Hz, 1H), 7.20-7.30 (buried m, 1H), 7.23 (d, J=8.0 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 18 h
  2. customevaporated to dryness
  3. customThe resultant residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with 1N HCl (2X), water (2X) and brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration
  7. customgave oil which
  8. customwas purified by flash chromatography on silica gel
  9. washElution of the column
  10. additionwith a mixture of hexane-ethyl acetate (7:3)

Sources & evidence

ORD record
ord-50106ea49df14ddaa3aba1e3672ea4f1
Source dataset
uspto-grants-1990_03
Patent number
US04906654

Reaction notes

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