Triethylamine → HCID 69737932, compound

Participants

Reaction Steps

A mixture of 3-aminomethylpiperidine-1-carboxylic acid tert-butyl ester (1.81 g, 8.47 mmol), [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (2.50 g, 8.47 mmol), triethylamine (2.4 mL, 16.9 mmol) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 68 hours. The mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate. The solution was washed with 1.0 N aqueous sodium hydroxide, then with water, then with saturated aqueous sodium chloride, and the organic phase was dried (sodium sulfate) and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 30% hexane in ethyl acetate, then with 25% hexane in ethyl acetate, to provide a white amorphous solid (3.19 g, 90%). 1H NMR (300 MHz, CDCl3) δ7.84 (s, 1H), 7.65 (d, J=8 Hz, 1H), 7.40 (t, J=8 Hz, 1H), 7.29 (d, J=7 Hz, 1H), 4.20 (s, 3H), 3.85 (m, 1H), 3.75 (m, 1H), 3.28 (dd, J=14, 5 Hz, 1H), 3.05 (m, 2H), 2.81 (dd, J=13, 9 Hz, 1H), 1.9-1.6 (m, 3H), 1.45 (s+m, 10H), 1.27 (m, 1H). Mass spec (AP+) m/z 416.2 (M+H+, 100%).

Provenance & Evidence