Potassium Hydroxide → HCID 20095322, compound

Participants

Reaction Steps

A solution of 1,3-dihydroisoindole [Bornstein, J.; Shield, J. E.; Boisselle, A. P. Organic Synthesis, Collective Vol 5; John Wiley & Son, Inc; New York, 1973, 406-408](2.30 g, 19.3 mmol), NaHCO3 (5.59 g, 66.6 mmol), and N-(2-chloroethyl)-N-methylbenzenemethanamine hydrochloride (4.25 g, 19.3 mmol) in anhydrous EtOH was refluxed overnight under an atmosphere of N2. The black, opaque mixture was filtered and the solids were washed with EtOH. The filtrate was concentrated to give a black slurry. The slurry was dissolved into a 1.0 N KOH solution (25 mL) and was extracted with EtOAc (3×10 mL). The combined organic layers were washed with a 5% NaHCO3 solution (10 mL), H2O (10 mL), and brine (10 mL) and then dried over MgSO4. The filtrate was concentrated in vacuo and purified by medium pressure column chromatography [silica gel, NH4OH:EtOH:CHCl3 (1:4:95)] to give the title compound as a black oil (2.22 g). The proton NMR spectrum was consistent with the proposed structure.

Provenance & Evidence