Isatin → HCID 23363889, compound

HRID 1081269Notes

Reaction equation

HRID 1081269 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[C:2]1=[O:11].[H-].[Na+].[Cl:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:19][CH2:18]1>CN(C=O)C>[ClH:14].[ClH:14].[CH:24]1([CH2:23][N:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3](=[O:10])[C:2]3=[O:11])[CH2:18][CH2:19]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 23363863HCID 23363863, compound

Product 1

HCID 23363889HCID 23363889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

1H-Indole-2,3-dione (2.4 g) in dry DMF (8 ml) at 0° C. was treated with sodium hydride (80% dispersion in mineral oil, 500 mg). The mixture was allowed to warm to room temperature and after 30 minutes 1-(2-chloroethyl)-4-(cyclohexylmethyl)piperazine (4 g) in dry DMF (8 ml) was added. The mixture was heated at 80° C. for 1.5 hours and then evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel and then treated with ethanolic HCl to give 1-[2-[4-(cyclohexylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione dihydrochloride, m.p. 256°-258° C.

Workup

  1. additionwas added
  2. customevaporated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel
  4. additiontreated with ethanolic HCl

Sources & evidence

ORD record
ord-7be431a69d3847999bbd39fe65707602
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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