Hydrochloric Acid → HCID 178511717, compound

Participants

Reaction Steps

To a solution of 9 g of trans-2-(4-phenylethyloxy-cyclohexyl)-isoindole-1,3-dione in 60 mL of THF and 150 mL of ethanol was added 3.75 mL of hydrazine hydrate and the mixture heated to reflux for 4 h, then 80 mL of 6N HCl was added and the reflux was continued for 1 h. The cooled mixture was concentrated under reduced pressure to remove ethanol and filtered. The filter pad was washed with 2×50 mL of dilute HCl and the combined filtrates basified to pH 10 with 20% sodium hydroxide and extracted with 3×150 mL portions of chloroform. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Further drying under vacuum gave 6 g of product as an oil. MS (m+1)=220.2; 1H NMR (400 MHz, CDCl3) 7.3-7.1 (m, 5H), 3.7 (t 2H), 3.2 (m, 1H), 2.9 (t, 2H), 2.7 (m, 1H), 2.0 (d, 2H), 1.85 (d, 2H), 1.4 (br s, 2H), 1.3 (dd, 2H), 1.15 (dd, 2H).

Provenance & Evidence