N-3-Bromopropylphthalimide → HCID 71224527, compound

HRID 710025Notes

Reaction equation

HRID 710025 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[NH4+:18].[Cl-]>CN(C=O)C>[CH3:9][CH:14]1[CH2:13][CH2:12][N:18]([CH2:4][CH2:5][CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 71224527HCID 71224527, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
12.5 °C

Procedure

To an ice-cold solution of NaH (0.505 g, 12.6 mmol) in DMF (20 mL) 5-methyl-pyrrolidin-2-one (1.0 g, 10.1 mmol) in DMF (10.0 mL) was added slowly. This was stirred for 30 min at 0-25° C. 2-(3-Bromo-propyl)-isoindole-1,3-dione (2.47 g, 9.0 mmol) was added and the reaction was stirred at room temperature for 16 h. A solution of saturated NH4Cl (10.0 mL) was added and extracted with ethyl acetate. Organic layer was washed with LiCl solution and concentrated. The crude was purified on silica gel using CH2Cl2/MeOH (10%) as eluent to give 2-[3-(3-methyl-2-oxo-pyrrolidin-1-yl)-propyl]-isoindole-1,3-dione (1.2 g, 41%).

Workup

  1. stirringthe reaction was stirred at room temperature for 16 h
  2. extractionextracted with ethyl acetate
  3. washOrganic layer was washed with LiCl solution
  4. concentrationconcentrated
  5. customThe crude was purified on silica gel

Sources & evidence

ORD record
ord-eb72436dabee47e1b04970943f4a13ab
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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