Hydrazine → HCID 67439310, compound

HRID 1664792Notes

Reaction equation

HRID 1664792 reaction equation
[NH2:1][NH2:2].[CH:3]1([C:6](=O)[CH2:7][CH:8]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[C:9](OCC)=[O:10])[CH2:5][CH2:4]1>C(O)(=O)C>[CH:3]1([C:6]2[CH2:7][CH:8]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])[CH2:16][CH2:15]3)[C:9](=[O:10])[NH:1][N:2]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67439783Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate

Product 1

HCID 67439310HCID 67439310, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine (0.3 mL, 9.6 mmol) was added to a solution of benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate (186 mg, 0.48 mmol) in acetic acid (7 mL). The reaction mixture was heated at 50° C. After 1 h, the reaction mixture was concentrated. The residue was diluted with dichloromethane and 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 356.2 (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-e88bc573afa44f55ba080029fdf18c01
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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