Ammonium Chloride → HCID 20277028, compound

Participants

Reaction Steps

5-Fluoro-3-(1-methyl-4-piperidyl)indanone (100 g) (prepared according to standard methods--J. Med. Chem., 11, (1968), 1064-66) in dry tetrahydrofuran (500 ml) was added dropwise to 4-fluorophenylmagnesium bromide (from 95 g of 4-bromofluorobenzene and 20 g of Mg-turnings in 500 ml of dry tetrahydrofuran). The reaction mixture was poured into NH4Cl (100 g) and crushed ice (3 L) and extracted with ether (2×300 ml). The combined organic phases were extracted with 0.5M CH3COOH (2×500 ml). The acid H2O-phase was made alkaline with 2M NaOH solution and extracted with ether (2×200 ml). The combined ether-phases were worked up as above and the starting material removed by washing with light petroleum. The title compound crystallized from isopropylether. Yield: 16.5 g (11.7%). MP: 148°-150° C.

Provenance & Evidence