Sodium Hydroxide → HCID 66628539, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(1-methyl-1H-indol-6-yl)[1,3,4]oxadiazole-2-thiol (1.25 g, 5.41 mmol), 1,4-Diazabicyclo[3.2.2]nonane (0.69 g, 5.41 mmol) and 1-propanol (5 ml) was stirred at 130° C. for 15 h. The reaction-mixture was allowed to cool to room-temperature. Aqueous sodium hydroxide (1 M) was added and the mixture was extracted twice with chloroform. The mixture was extracted twice with aqueous hydrochloric acid. The aqueous phase was washed with chloroform and was made alkaline by adding sodium hydroxide (4 M), followed by extraction three times with chloroform. The free base was isolated as a brown oil. Yield 500 mg (29%) The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 250 mg (36%). LC-ESI-HRMS of [M+H]+ shows 324.1823 Da. Calc. 324.182435 Da, dev. −0.4 ppm.

Provenance & Evidence