Succinimide → N-(2-cycloheptenyl)succinimide

HRID 247621Notes

Reaction equation

HRID 247621 reaction equation
Br[CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.[C:9]1(=[O:15])[NH:13][C:12](=[O:14])[CH2:11][CH2:10]1.[Na].C1(=O)NC(=O)CC1.[H-].[Na+]>O.CN(C=O)C>[CH:2]1([N:13]2[C:9](=[O:15])[CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 11439SuccinimideHCID 24758Sodium hydrideHCID 124538813-Bromocyclohept-1-eneHCID 66769941Sodium succinimide

Product 1

HCID 13506505N-(2-cycloheptenyl)succinimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Bromocycloheptene (1.75 g) was added dropwise at room temperature to a DMF suspension (10 ml) of sodium succinimide prepared from succinimide (0.99 g) and 60% sodium hydride (0.40 g). This mixture was stirred at room temperature for 24 hours, poured into water (10 ml) and extracted with ether. The oily product obtained by concentration was purified by chromatography on silica gel to obtain 0.09 g of N-(2-cycloheptenyl)succinimide [Compound (214)].

Workup

  1. extractionextracted with ether
  2. customThe oily product obtained by concentration
  3. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-76c9c1ca543841c883d77550d87dbfde
Source dataset
uspto-grants-1987_11
Patent number
US04709052

Reaction notes

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