1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 18467245, compound

HRID 611938Notes

Reaction equation

HRID 611938 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:2]1.Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)(O)[O-].[Na+]>C(#N)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:17][CH2:18][N:19]3[C:23](=[O:24])[C:22]4=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]4[C:20]3=[O:29])[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 516892Sodium BicarbonateHCID 148234453-(Piperazin-1-YL)-1H-indazole

Product 1

HCID 18467245HCID 18467245, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(1H-indazol-3-yl)piperazine (1.6 g, 7.9 mmol), N-(2-bromoethyl)phthalimide (2.1 g, 7.9 mmol), and sodium bicarbonate (0.7 g, 8.3 mmol) in acetonitrile (160 ml) was warmed to reflux for 24 hours. Upon cooling to room temperature, the reaction mixture was filtered through a pad of celite and the solids were washed with DCM. The combined filtrates were concentrated to give the N-[2-[4-(1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide which was used without further purification.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux for 24 hours
  3. filtrationthe reaction mixture was filtered through a pad of celite
  4. washthe solids were washed with DCM
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-a86c84c2f87e45d99bb2ab186966bc45
Source dataset
uspto-grants-1999_12
Patent number
US06001834

Reaction notes

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