Triethylamine → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-4,6-bis(trifluoromethyl)benzamide

Participants

Reaction Steps

A mixture of 2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride and methyl 2,4-bis(trifluoromethyl)benzoate (approximately 0.5 mmol) prepared as described in D53 was dissolved in dry DCM (3 ml) and treated with (+)-{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (109 mg, 0.50 mmol) and triethylamine (140 ul, 1.00 mmol) and left overnight at room temperature. The volatile components were removed under reduced pressure and the residue chromatographed on silica gel. Elution with 0-80% ethyl acetate in pentane gave the title product (86 mg, ca.36%). 1H NMR (CDCl3) δ: 0.95 (1H, br m), 1.44-1.86 (7H, overlapping m), 2.20 (6H, s), 2.41 (3H, br s), 5.10 (1H, d, J=5.6 Hz), 7.07 (1H, br s), 7.26-7.42 (5H, overlapping m), 7.67 (1H, s), 7.77 (1H, s). Mass Spectrum (Electrospray LC/MS): Found 473 (MH+) C24H26F6N2O requires 472. Ret time 2.25 min.

Provenance & Evidence