Sodium hydride → HCID 59238195, compound

Participants

Reaction Steps

4-(1H-Indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (8.50 g) was stirred in 70 mL of DMF and cooled with an ice/water bath. To this mixture sodium hydride (1.35 g of 60% dispersion in mineral oil) was added in portions. After addition was completed, the mixture was stirred for 30 minutes at 0° C. before the addition of 7.15 g of bromo-acetic acid tert-butyl ester. The reaction mixture was allowed to reach room temperature while stirring for 2 hours. At this time, brine was added to the mixture; ethyl acetate was used for extraction of the organic soluble components. The organic layer was washed with water four times, then dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo leaving a reddish oil which was dissolved in 70 mL of hexane. Upon standing for 3 days, a precipitate formed. After filtration and washing of the precipitate with pentane, the solid was dried. In this manner, 8.85 g of the desired product was obtained. H1-NMR spectroscopy indicated a spectrum consistent with 4-(1-tert-butoxycarbonylmethyl-1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence