Hydrazine hydrate (1:1) → 2-[2-(2-oxo-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 1787693Notes

Reaction equation

HRID 1787693 reaction equation
ClC[C:3]([N:5]([CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])[CH2:6][CH2:7][N:8]1[C:16](=O)C2C(=CC=CC=2)C1=O)=[O:4].O.NN>CCO>[O:4]=[C:3]1[CH2:16][NH:8][CH2:7][CH2:6][N:5]1[CH2:19][CH2:20][N:21]1[C:22](=[O:31])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]1=[O:30]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 684562152-chloro-N,N-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]acetamide

Product 1

HCID 684533342-[2-(2-oxo-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dioneYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-N,N-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]acetamide (2 g, 4.55 mmol) in EtOH (230 mL) was added hydrazine hydrate (213 μL, 6.83 mmol). After 12 h at 85° C., the solution was concentrated and the residue purified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH)) yielding the title compound (428 mg, 34%) as a yellow foam: LCMS (ES) m/e 274 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue purified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-671a451267fd4c81a29411df3da2926a
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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