(3-Bromopropyl)benzene → HCID 131715160, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4.08 g (0.018 m) of cis-1,2,3,4,4a,9b-hexahydro-4a-(2-methylaminoethyl)dibenzofuran of Example 11 and 4.38 g (0.022 m) of 1-bromo-3-phenylpropane in 60 ml DMF, 3.8 g (0.045 m) of NaHCO3 was added under nitrogen. The reaction mixture was warmed to 87° C. and held there overnight (about 16 hours). The temperature was raised to 108° C. for 4 hours, the NaHCO3 filtered off and the mixture partitioned between water and ethyl acetate. The ethylacetate layer was dried over Na2SO4 and evaporated to give an oil. The resultant oil was converted to an oxalate in ether as in Example 4 and recrystallized from ethyl acetate to give 2.2 g (28%) of cis-1,2,3,4,4a,9b-hexahydro-4a-[2-[-N-(3-phenylpropyl)-N-methylamino]ethyl]dibenzofuran oxalate hemihydrate m.p. 104°-105° C.

Provenance & Evidence