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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.

1. customOrganic Synthesis, Collective Vol 5
2. filtrationThe black, opaque mixture was filtered
3. washthe solids were washed with EtOH
4. concentrationThe filtrate was concentrated
5. customto give a black slurry
6. extractionwas extracted with EtOAc (3×10 mL)
7. washThe combined organic layers were washed with a 5% NaHCO3 solution (10 mL), H2O (10 mL), and brine (10 mL)
8. dry with materialdried over MgSO4
9. concentrationThe filtrate was concentrated in vacuo
10. custompurified by medium pressure column chromatography [silica gel, NH4OH:EtOH:CHCl3 (1:4:95)]