Ethyl chloroformate → (N-1-azabicyclo[2.2.2]oct-3-yl)-7-chloro-4-methoxy-2,3-dihydroindole-5-carboxamide

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Reaction Conditions

Reaction Steps

Ethyl chloroformate (25 ml) is added to a stirred mixture of the acid compound of step 10 above (0.7 g) in CHCl3 -Et3N (25 ml/0.7 g) chilled to -20° C. and stirring is continued for one hour. Aminoquinuclidine (2.8 g) and a saturated aqueous K2CO3 solution (7 ml) are added to the reaction mixture. Stirring is continued for 2 hours while slowly warning to RT. The mixture is diluted with CHCl3 and H2O, stirred for 5 minutes and the aqueous layer was separated. The organic layer is washed with H2O, dried (MgSO4) and evaporated affording a foamy solid which is converted to the dihydrochloride salt by dissolving in HCl-MeOH and evaporating the solvent. The desired product in the form of the dihydrochloride salt is a hygroscopic material is determined to be the correct material by NMR. M.P.=151°-153° C. Elemental Analysis: Calc'd C: 49.95, H 5.92, N 10.28; Found C: 50.58, H 6.20, N 9.98.

Provenance & Evidence