4-Fluorophenylhydrazine hydrochloride → 9-Benzyl-3-(4-fluoro-phenyl)-3,4,9-triaza-tricyclo[5.3.1.02,6]undeca-2(6),4-diene

HRID 272619Notes

Reaction equation

HRID 272619 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([C:11](=[CH:17][N:18](C)C)[C:12]2=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29]N)=[CH:25][CH:24]=1>C(O)C>[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([C:11]3[CH:17]=[N:18][N:29]([C:26]4[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=4)[C:12]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 688083373-Benzyl-7-dimethylaminomethylene-3-aza-bicyclo[3.2.1]octan-6-one

Product 1

HCID 598378509-Benzyl-3-(4-fluoro-phenyl)-3,4,9-triaza-tricyclo[5.3.1.02,6]undeca-2(6),4-dieneYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-benzyl-7-dimethylaminomethylene-3-aza-bicyclo[3.2.1]octan-6-one (0.6 mmol) in ethanol (3 mL) was added (4-fluoro-phenyl)-hydrazine hydrochloride (0.7 mmol). The reaction mixture was heated at reflux overnight, cooled, concentrated and the residue was treated with dichloromethane and aqueous sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane and the organic layer was dried and stripped to provide an oil that was purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes to yield product (0.23 mmol). 1H NMR (CDCl3, 400 MHz) δ 7.55 (m, 2H), 7.40 (s, 1H), 7.20–6.90 (m, 7H), 3.50 (br s, 2H), 3.25 (br s, 1H), 3.10 (br s, 1H), 2.95–2.6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionthe residue was treated with dichloromethane and aqueous sodium bicarbonate solution
  6. extractionThe aqueous layer was extracted with dichloromethane
  7. customthe organic layer was dried
  8. customto provide an oil that
  9. customwas purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9df996e909c1490199e9e2e7dadebaea
Source dataset
uspto-grants-2008_11
Patent number
US07456177B2

Reaction notes

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