Triethylamine → HCID 59347777, compound

Participants

Reaction Steps

To a solution of (+)-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine D6 (0.10 g; 0.459 mmol) and triethylamine (0.15 ml; 1 mmol) in DCM (3 ml) was added a solution of 2,4-dichloro-6-methyloxybenzoyl chloride (0.13 g; 0.540 mmol) in DCM (2 ml). After 1 h. saturated aqueous sodium hydrogen carbonate (8 ml) was added and the mixture shaken for 2 minutes. The organic layer was passed through a phase separation cartridge and the solvent removed under reduced pressure. The residue was dissolved in the minimum of DCM and applied to a 10 g silica gel column. Elution with 0-100% ethyl acetate in pentane gradient and removal of solvent under reduced pressure afforded the title compound as a colourless gum (0.14 g: 72%). 1H NMR (CDCl3) δ: 0.91 (3H, s), 0.96 (3H, s), 1.60-1.80 (4H, m), 2.55-2.75 (4H, m), 3.82 (3H, s), 4.76 (1H, d, J=2.4 Hz), 6.81 (1H, d, J=1.6 Hz), 7.02 (1H, d, J=1.6 Hz), 7.20-7.50 (6H, m). Mass spectrum (Electrospray LC/MS). Found 421 (MH+). C22H2635Cl2N2O2 requires 420. Ret. Time: 1.97 min.

Provenance & Evidence