Diethyl Ether → HCID 178514305, compound

HRID 539627Notes

Reaction equation

HRID 539627 reaction equation
[C:1]1([CH:7]2[NH:12][C:11](=O)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O(C)S(C(F)(F)F)(=O)=O.[NH2:23][NH2:24].C(OCC)C>C(Cl)Cl.CO>[C:1]1([CH:7]2[NH:12]/[C:11](=[N:23]\[NH2:24])/[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 9526Methyl triflateHCID 6002256-phenylpiperidin-2-one

Product 1

HCID 178514305HCID 178514305, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 6-phenyl-piperidin-2-one (0.35 g, 2 mmol) in methylene chloride (1 mL) at 0° C. under nitrogen atmosphere was added methyl triflate (0.23 mL, 2 mmol). The reaction mixture was stirred at room temperature for three hours, then added to a stirring 0°C solution of anhydrous hydrazine (0.5 mL) in methanol (1 mL). The mixture was stirred for 3.5 hours at room temperature, then poured into a 1:1 mixture of methylene chloride and diethyl ether. The mixture was washed with 1.5M aqueous sodium carbonate, dried over anhydrous potassium carbonate, filtered, and concentrated under reduced pressure to give 0.34 g (90%) of [6-phenyl-piperidin-(2Z)-ylidene]-hydrazine as a colorless oil.

Workup

  1. stirringThe mixture was stirred for 3.5 hours at room temperature
  2. washThe mixture was washed with 1.5M aqueous sodium carbonate
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-080bf0fe84174f2397ef27543965a91e
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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