Hydrazine hydrate (1:1) → HCID 54579447, compound

HRID 75483Notes

Reaction equation

HRID 75483 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:11][CH2:10]1.O.NN>CCO>[ClH:1].[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 545794462-(3-(4-(2,3-Dichlorophenyl)piperazin-1-yl)propyl)isoindoline-1,3-dione2×

Product 1

HCID 54579447HCID 54579447, compoundYield 218.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)isoindoline-1,3-dione (compound 36, 11.1 g, 26.5 mmol) in EtOH was added hydrazine monohydrate. The reaction mixture was stirred at room temperature for 6 hrs, then the white solid filtered off. The filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. To the crude product in diethyl ether was added 2M HCl solution in diethyl ether (10 mL). The obtained product was washed with diethyl ether to provide the title compound (6.98 g, 73%) as a white solid.

Workup

  1. filtrationthe white solid filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionTo the crude product in diethyl ether was added 2M HCl solution in diethyl ether (10 mL)
  9. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-7f9dffd5082645659510d497d4b3ce62
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

Loading…