Isatin → HCID 23363840, compound

HRID 1081270Notes

Reaction equation

HRID 1081270 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[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>CN(C=O)C>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:20]2[CH2:19][CH2:18][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])[CH2:22][CH2:21]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 23363873HCID 23363873, compound

Product 1

HCID 23363840HCID 23363840, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

1H-Indole-2,3-dione (2.9 g) in dry DMF (5 ml) at 0° C. was treated with sodium hydride (80% dispersion in mineral oil, 600 mg). The mixture was warmed to 40° C. and after 45 minutes a solution of 1-(2-chloroethyl)-4-[(4-fluorophenyl)methyl]piperazine (5.1 g) in dry DMF (8 ml) was added. The reaction mixture was heated at 80° C. for 5 hours and then evaporated under reduced pressure. The residue was recrystallised twice to give 1-[2-[4-[(4-fluorophenyl)methyl]-1-piperazinyl]ethyl]-1H-indole-2,3-dione, m.p. 146°-147° C.

Workup

  1. additionwas added
  2. customevaporated under reduced pressure
  3. customThe residue was recrystallised twice

Sources & evidence

ORD record
ord-09ff7a381dd94e72812a7a24d2a9b4f5
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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