Chlorosuccinimide → HCID 19769404, compound

HRID 1590047Notes

Reaction equation

HRID 1590047 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][NH:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:32])[N:16]([CH:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)[C:17](=[O:24])[C:18]3[C:23]=2[C:22]=1[CH:21]=[CH:20][CH:19]=3>CN(C)C=O>[Cl:1][C:12]1[C:11]([NH:10][CH3:9])=[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:23]2=[C:14]([CH:13]=1)[C:15](=[O:32])[N:16]([CH:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)[C:17]3=[O:24]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 19769371HCID 19769371, compound

Product 1

HCID 19769404HCID 19769404, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of N-chlorosuccinimide (0.255 g; 1.90 mmol) and 2,3-dihydro-6-methylamino-2-(1-methylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione (0.65 g; 1.80 mmol), prepared as in Example 5, in N,N-dimethylformamide (12 mL) was stirred approximately 72 hours. The solvent was removed and acetone (approximately 25 mL) was added to the residue. The acetone mixture was heated to boiling and then stirred for 1 hour at room temperature. The solid was collected from the mixture, stirred again in acetone, and recollected. Drying under vacuum gave 5-chloro-2,3-dihydro-6-methylamino-2-(1-methylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione (0.65 g; 1.65 mmol), m.p. 298°-302° C.

Workup

  1. customThe solvent was removed
  2. additionacetone (approximately 25 mL) was added to the residue
  3. temperatureThe acetone mixture was heated
  4. customThe solid was collected from the mixture
  5. stirringstirred again in acetone
  6. customDrying under vacuum

Sources & evidence

ORD record
ord-ac8a0877ad994b95890085141cab15a5
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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