Hydrazine hydrate (1:1) → HCID 178507308, compound

HRID 1747490Notes

Reaction equation

HRID 1747490 reaction equation
O.[NH2:2][NH2:3].O=[C:5]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)[CH2:6][C:7]#[N:8]>C(O)C>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:12]1[CH2:11][CH2:10][CH:9]([C:5]2[CH:6]=[C:7]([NH2:8])[NH:3][N:2]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118020339HCID 118020339, compound

Product 1

HCID 178507308HCID 178507308, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.20 mL, 4.12 mmol) was added to a solution of 3-oxo-3-[1-(pyridin-2-yl)piperidin-4-yl]propanenitrile (138 mg, 0.60 mmol) produced in Reference Example 1 in ethanol (20 mL), and the mixture was stirred for 5 hours under heating to reflux. The reaction solution was left until reaching room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=100/0-94/6 (gradient)] to obtain the title compound (130 mg, yield: 89%).

Workup

  1. temperatureunder heating to reflux
  2. waitThe reaction solution was left
  3. customuntil reaching room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=100/0-94/6 (gradient)]

Sources & evidence

ORD record
ord-4479970fbd0d45fd894366850a696be0
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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