Hydrazine → HCID 67439796, compound

HRID 1664786Notes

Reaction equation

HRID 1664786 reaction equation
[NH2:1][NH2:2].C[O:4][C:5]([CH:7]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1)[CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O>C(O)(=O)C>[O:4]=[C:5]1[CH:7]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH2:18]2)[CH2:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:2][NH:1]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67440013HCID 67440013, compound

Product 1

HCID 67439796HCID 67439796, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine (3.31 mL, 104 mmol) was added to a solution of benzyl 4-[1-(methoxycarbonyl)-3-oxo-3-phenylpropyl]piperidine-1-carboxylate (2.14 g, 5.22 mmol) in acetic acid (70 mL). The reaction mixture was heated at 50° C. After 1 h, the reaction mixture was concentrated. The residue was diluted with dichloromethane, neutralized by saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were dried over magnesium sulfate and concentrated to give the title compound. MS 392.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was diluted with dichloromethane
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bdd26fc8f934b8699f5d6abbb3430dd
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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