Hydrazine hydrate (1:1) → HCID 15712603, compound

HRID 2400628Notes

Reaction equation

HRID 2400628 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:4][CH2:3]1.O.NN>C(O)C.C(Cl)Cl>[NH2:9][O:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15712604HCID 15712604, compound

Product 1

HCID 15712603HCID 15712603, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(1-methylpiperidin-4-yl)oxy]-1H-isoindole-1,3(2H)-dione 49 (1.18 g, 4.53 mmol) in a mixture of ethanol (3 mL) and DCM (18 mL) was added hydrazine hydrate (0.268 g, 4.53 mmol). The reaction mixture was stirred at room temperature for 4.5 h. Precipitate was filtered off. The filtrate was evaporated and sonicated in ethyl acetate (20 mL). Solid was filtered off and filtrate was evaporated to give the residue which was subjected to chromatography to give 50 (0.15 g, 25%) as a colorless oil.

Workup

  1. filtrationPrecipitate was filtered off
  2. customThe filtrate was evaporated
  3. customsonicated in ethyl acetate (20 mL)
  4. filtrationSolid was filtered off
  5. customfiltrate was evaporated
  6. customto give the residue which

Sources & evidence

ORD record
ord-da15494f7c294d3cac8aa4690c4ab1f1
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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