Benzocaine → HCID 22600032, compound

Participants

Reaction Steps

A solution of phenethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (9) (619 mg, 2.01 mmole) in 10 mL toluene was treated with 1.5 mL of a 20% phosgene solution in toluene and stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, the residue diluted with 15 mL of pyridine and then treated with 665 mg of ethyl p-aminobenzoate (2 eq.). The mixture was heated at 40° C. for 15 hours, then concentrated in vacuo to provide an orange oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes, dry pack) to yield 441 mg (44%) of ethyl 4-[3-phenethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (11) as a pale yellow foam.

Provenance & Evidence