HCID 19980025, compound → HCID 19019967, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of (4-aminophenyl)-(6-hydroxyhexyl)sulfone (Example 5, 7.2 g, 28 mmol) in 60 mL of 10% HCl was cooled to 0° C. and treated dropwise with 2.1 g (31 mmol) of sodium nitrite in 10 mL of water. The reaction mixture was stirred for 15 minutes and 7.8 g (28 mmol) of butyl N-methyl-N-phenyl-6-aminohexanoate (Example 2) was added slowly. The resulting mixture was gradually warmed to 23° C. and then stirred for 16 hours. The precipitated solid was filtered, washed with water, and air dried. The product was purified by flash chromatography on silica gel, eluting with 20% (v/v) ethyl ether/80% dichloromethane. The eluate was concentrated at reduced pressure and the residue was recrystallized from toluene/heptane to yield 8.1 g (53%) of an orange powder.

Provenance & Evidence