Benzenemethanamine, 3,4-dichloro- → HCID 58460223, compound

Participants

Reaction Steps

A solution of Intermediate 45 (600 mg), ammonium acetate (233 mg), 3,4-dichlorobenzylamine (0.484 mL), acetic acid (0.866 mL) and isobutyraldehyde (0.276 mL) in chloroform (6 mL) was heated to 65° C. The reaction was heated for 21 hr, after which time the reaction mixture was partitioned between ethyl acetate (100 mL) and 1 M NaOH aqueous soln. (100 mL). The organic layer was separated and the aqueous layer extracted with further DCM (1×100 mL). The combined organic layers were filtered through a hydrophobic frit and conc. in vacuo to afford 1.18 g of crude product. The crude product was purified by flash column chromatography (silica, 0-100% cyclohexane/ethyl acetate) to afford the desired regioisomer (250 mg). LC/MS MH+ 409/411/413, Rt 2.47 min (5 min run).

Provenance & Evidence