Phenylhydrazine → HCID 58123978, compound

HRID 1519209Notes

Reaction equation

HRID 1519209 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-61ecf21d1114438d9b5ab9e30bfb3649
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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