Sodium Hydroxide → HCID 22633667, compound

Participants

Reaction Steps

600 mg of butyl 3-[(octahydro-4,7-methanoinden-5-ylamino)methyl]benzoate were dissolved in 1 ml of n-butanol, and 2.1 ml of a 1 N aqueous NaOH solution were added. The mixture was stirred at RT for 18 hours and then at 60° C. for 4 hours. The volatile components were then removed under reduced pressure and residual n-butanol was then distilled off twice, azeotropically, under reduced pressure, using in each case 5 ml of water. The residue was taken up in 5 ml of a 10% strength aqueous HCl solution, the volatile components were removed under reduced pressure, and the water was distilled off azeotropically twice, under reduced pressure, using in each case 5 ml of toluene. Since the product still contained considerable amounts of starting material, it was once more dissolved, in 6 ml of methanol, and admixed with 1 ml of a 2 N aqueous NaOH solution. The mixture was stirred at RT for 3 hours, and a further 5 ml of a 2 N aqueous NaOH solution were then added and the mixture was boiled under reflux for 4 hours. The volatile components were removed under reduced pressure, the residue was taken up in 20 ml of water, and the mixture was adjusted to pH=7 using dilute aqueous HCl solution. The mixture was stirred at RT for 1 hour and the product was filtered off with suction and dried under reduced pressure. This gave 260 mg of a crystalline solid, mp 258-261° C.

Provenance & Evidence