Phenylhydrazine → HCID 58123978, compound

HRID 536658Notes

Reaction equation

HRID 536658 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH:9]1[CH2:10][CH2:11][C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([NH:24]N)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH:9]1[CH2:10][C:11]1[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH:24][C:12]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 11430Potassium CarbonateHCID 58123994HCID 58123994, compound

Product 1

HCID 58123978HCID 58123978, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2-benzyl-2-aza-bicyclo[3.3.1]nonan-6-one in acetic acid (0.24 g) is added to a solution of PhNHNH2*HCl (173 mg) in acetic acid (4 mL) heated at reflux temperature. After stirring at this temperature for 2 h, the solution is cooled to room temperature and aqueous K2CO3 solution is added. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are dried (Na2SO4), and the solvent is removed. The residue is purified by HPLC on reversed phase (MeCN/water).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. dry with materialthe combined organic extracts are dried (Na2SO4)
  5. customthe solvent is removed
  6. customThe residue is purified by HPLC on reversed phase (MeCN/water)

Sources & evidence

ORD record
ord-9ec08af33872446393c515ebc66b2821
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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