Triethylamine → 1'-[(6-Chloro-1H-indol-3-yl)carbonyl]spiro[isoindole-1,4'-piperidin]-3(2H)-one

To a solution of 0.060 g (0.31 mmol) 6-chloro-1H-indole-3-carboxylic acid in 3 ml dichloromethane were added 0.045 ml (0.38 mmol) 1-chloro-N,N,2-trimethyl-propenylamine at room temperature. After stirring for 1 h the reaction mixture was concentrated in vacuo. The residue was redissolved in 2 ml dry N,N-dimethylformamide. A solution of 0.062 g (0.31 mmol) spiro[isoindole-1,4′-piperidin]-3(2H)-one and 0.064 ml (0.46 mmol) triethylamine in 1 ml dry N,N-dimethylformamide was added at room temperature. After stirring for 2 h the reaction mixture was quenched with 1 M aqueous sodium hydroxide solution (30 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with water (2×30 ml), 0.5 M aqueous hydrochloric acid solution (1×30 ml) and brine (1×30 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was triturated in warm diethyl ether, filtrated and dried in vacuo to give the title compound (0.031 g, 22%) as light brown solid with a purity of approx. 80% by LC-.MS.

1. concentrationwas concentrated in vacuo
2. dissolutionThe residue was redissolved in 2 ml dry N,N-dimethylformamide
3. stirringAfter stirring for 2 h the reaction mixture
4. customwas quenched with 1 M aqueous sodium hydroxide solution (30 ml)
5. extractionextracted with ethyl acetate (3×50 ml)
6. washThe combined organic layers were washed with water (2×30 ml), 0.5 M aqueous hydrochloric acid solution (1×30 ml) and brine (1×30 ml)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe crude product was triturated in warm diethyl ether
10. filtrationfiltrated
11. customdried in vacuo

ORD-Eintrag

ord-b289855f63794137997bcf595ff314c0

Quelldatensatz

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07332501B2