5-Methylisatin → 5-Methyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione Dihydrochloride

HRID 1081267Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].[Cl:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>CN(C=O)C>[ClH:15].[ClH:15].[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]1)[C:6](=[O:11])[C:5]2=[O:12]

Participants

Conditions

Temperature: 70 °C

Procedure

5-Methyl-1H-indole-2,3-dione (12.85 g) in dry DMF (50 ml) at 0° to 5° C. was treated with sodium hydride (80% dispersion in mineral oil, 2.53 g). The mixture was allowed to warm to room temperature and after a further 10 minutes 1-(2-chloroethyl)-4-(phenylmethyl)piperazine (20 g) in dry DMF (70 ml) was added. The mixture was heated at 70° C. for 3 hours and then evaporated under reduced pressure. The residue was subjected to flash chromatography on silica gel to afford the title compound (17.75 g). Treatment with ethanolic HCl then gave 5-methyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione dihydrochloride (16.8 g), m.p. 270°-275° C. (dec.).

Workup

additionwas added
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c74420ad9f1d4133af56c117b3d5c11d
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585378

Reaction notes

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