Sodium hydride → 1,3-Dihydro-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-2H-indol-2-one

HRID 1081273Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:12].Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1>CN(C=O)C>[C:23]1([CH2:22][N:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][N:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:5][C:4]3=[O:12])[CH2:17][CH2:18]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (80% dispersion in mineral oil, 250 mg) was added to a solution of 1,3-dihydro-2H-indol-2-one (1.12 g) in dry DMF (5 ml at 0° C. The mixture was allowed to warm to room temperature and after 50 minutes a solution of 1-(2-chloroethyl)-4-(phenylmethyl)piperazine (2.02 g) in dry DMF (6 ml) was added. The reaction mixture was then heated at 80° C. for 2 hours and then evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on silica gel to afford the title compound (1.1 g, 40%) as an oil.

Workup

additionwas added
customevaporated to dryness under reduced pressure
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-a86d286f0df745eab3711224728a5bff
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585378

Reaction notes

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