Diisopropylethylamine → HCID 86666752, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 0.32 g (1.3 mmol) of tert-butyl bis(2-chloroethyl)carbamate in 5 ml of N,N-diisopropylethylamine and 0.5 mL of anhydrous N,N-dimethylformamide was added 0.23 g (1.1 mmol) of 1-pyridin-2-ylcyclopropanamine, bis(hydrochloride) salt and the resulting mixture was heated to 100° C. for 15 h. The mixture was cooled to ambient temperature, quenched with water, and the aqueous phase extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography eluting with 50% acetone/hexanes mixture to afford the title compound as yellow gum (0.055 g, 17% yield). 1H-NMR (500 MHz, CDCl3) δ 8.55 (d, J=4.7 Hz, 1H), 7.61 (td, J=7.7, 1.7 Hz, 1H), 7.33 (d, J=7.9, 4.6 Hz, 1H), 7.12 (dd, J=7.4, 4.9 Hz, 1H), 3.37-3.35 (m, 4H), 2.60-2.58 (m, 4H), 1.41 (s, 9H), 1.05-1.03 (m, 4H). LC-MS: m/z (ES) 304.5 (MH)+.

Provenance & Evidence