Triethylamine → Imipramine

Participants

Reaction Steps

6-Carboxyfluorescein (1.00 g, 2.66 mmol) was dissolved in 8 mL DMF, 306 mg (2.66 mmol) of N-hydroxysuccinimide was added, 549 mg (2.66 mmol) of 1,3-dicyclohexylcarbo-diimide was added, and the reaction stirred for 17 hours, under N2, in the dark. The reaction mixture was vacuum filtered, filtrate combined with 7.84 mg (2.65 mmol) of 2-aminoimipramine (4c), 0.56 mL (4.0 mmol) of triethylamine, and 4.0 mL DMF, and reaction allowed to stir 4 days under N2, in the dark. Reaction solvents were removed in vacuo and residue purified on reverse phase C18 semi-preparative (1 mm) TLC plates, eluting with H2O/THF/HOAc (40/60/0.4) followed by preparative HPLC on a Waters mbondapak C18 column (19 mm× 150 mm), eluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute to yield 410 mg (24%) of the desired imipramine tracer (12) as an orange powder; mass spec (FAB) (M+H)+ 654.

Provenance & Evidence