Tetrahydrofuran → HCID 60134491, compound

Participants

Reaction Steps

Crude N1-(3-(Dimethylamino)propyl)-N1,3-dimethylbutane-1,3-diamine (18.0 g, 31.9 mmol) was dissolved into THF (200 mL). Sodium hydrogen carbonate (14.0 g, 0.167 mol) dissolved in water (200 mL) was added to reaction to give a solution. CbzOSu (7.95 g, 1 equiv, 31.9 mmol) was added in one portion to the reaction and left to stir at room temperature for 16 h. The organic solvent was removed via rotovap and the aqueous concentrated to ˜100 mL. The aqueous was extracted with DCM (2×200 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. The desired fractions were collected and lyophilized to give a colorless oil (5.57 g, yield: 52.1%). LRMS (ESI+) for C19H33N3O2 (335.3); Found: 336 (MH+).

Provenance & Evidence