Hydrazine hydrate (1:1) → HCID 59888385, compound

HRID 732939Notes

Reaction equation

HRID 732939 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:4][CH2:3]1.O.NN>CCO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68657650HCID 68657650, compound

Product 1

HCID 59888385HCID 59888385, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-[4-(1-methyl-piperidin-4-yl)-butyl]-isoindole-1,3-dione (2.67 g, 8.89 mmol) in EtOH (50 mL) was added excess hydrazine hydrate (15 mL). After 18 h, the mixture was filtered and the filtrate was diluted with satd aq. NaHCO3 (20 mL) and water (20 mL). The mixture was extracted with CHCl3 (3×50 mL) and the combined organic layers were dried (Na2SO4) and concentrated to provide 1.36 g (90%) of a yellow oil, which was used in the next step without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. additionthe filtrate was diluted with satd aq. NaHCO3 (20 mL) and water (20 mL)
  3. extractionThe mixture was extracted with CHCl3 (3×50 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c947813b98748b7afe81740b905d51a
Source dataset
uspto-grants-2009_09
Patent number
US07589087B2

Reaction notes

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