Potassium Hydroxide → HCID 86754004, compound

HRID 1420087Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:3]1.[OH-].[K+].Br[CH2:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1>CS(C)=O.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:21][CH2:22][O:23][C:24]3[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=3)[CH2:14][CH2:13]2)=[CH:3]1

Participants

Conditions

Temperature: 22 °C

Procedure

A suspension of 1-(1-methylindole-3-ylmethyl)piperazine (1.3 g) in dimethylsulfoxide (15 ml) and potassium hydroxide (0.63 g) was stirred for 30 min under nitrogen at 22° C. and then a solution of 4-[2-bromoethoxy]benzaldehyde (1.3 g) was added and stirring was continued for further 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate and the organic layer was washed with water, brine, dried (Na2SO4) and solvent was evaporated under reduced pressure. The crude product was chromatographed on silica gel using mixture of methanol: chloroform (1:9) as eluent to afford the pure product (0.76 g, 51%) as an oil.

Workup

stirringstirring
waitwas continued for further 4 h
extractionextracted with ethyl acetate
washthe organic layer was washed with water, brine
dry with materialdried (Na2SO4) and solvent
customwas evaporated under reduced pressure
customThe crude product was chromatographed on silica gel using mixture of methanol: chloroform (1:9) as eluent

Sources & evidence

ORD record: ord-aed4d31a16ec446a9e72ad126b3db624
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889032

Reaction notes

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