Sodium hydride → 4,7-dimethyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione dihydrochloride

HRID 1081271Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.[H-].[Na+].[Cl:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1>CN(C=O)C>[ClH:16].[ClH:16].[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[N:6]2[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

4,7-Dimethyl-1H-indole-2,3-dione (700 mg) in dry DMF (10 ml) was cooled to 0° C. and sodium hydride (80% dispersion in mineral oil, 120 mg) was added. After 30 minutes at 0° C. 1-(2-chloroethyl)-4-(phenylmethyl)piperazine (1 g) in dry DMF (5 ml) was added. The mixture was heated to 80° C. for 2 hours and then evaporated under reduced pressure. The residue was subjected to flash chromatography and then treated with ethanolic HCl to give 4,7-dimethyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione dihydrochloride, m.p. 223°-227° C. (dec.).

Workup

customevaporated under reduced pressure
additiontreated with ethanolic HCl

Sources & evidence

ORD record: ord-4cf0ee6898e54ce390f7a8983b1dd722
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585378

Reaction notes

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