Reaktion #49111

Reaktionsgleichung

4-fluoro-2,6-dimethylbenzoyl chloride

{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

triethylamine

→

title compound

Ausbeute 100.0%

N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-4-fluoro-2,6-dimethylbenzamide

Ausbeute 100.0%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenAfter 16 h. the reaction was washed with water
2. 2
   Trocknendried with MgSO4
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe residue was chromatographed on silica gel eluting with an ethyl acetate-hexane 0 to 100% gradient

Vorschrift

To {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (0.904 g; 4.147 mmol) in DCM (45 ml) under argon at room temperature was added triethylamine (0.573 ml; 4.15 mmol), followed by a solution of 4-fluoro-2,6-dimethylbenzoyl chloride (0.773 g: 4.144 mmol) in DCM (5 ml). After 16 h. the reaction was washed with water, dried with MgSO4 and evaporated. The residue was chromatographed on silica gel eluting with an ethyl acetate-hexane 0 to 100% gradient to give the title compound (1.57 g; 100%). 1H NMR (CDCl3) δ: 0.85-1.00 (1H, m), 1.30-1.60 (3H, m), 1.60-1.75 (2H, m), 1.75-1.90 (2H, m), 2.22 (6H, s), 2.31 (6H, m), 5.18 (1H, d, J=6 Hz), 6.73 (2H, d, J=9.6 Hz overlaps 1H, br s), 7.20-7.35 (3H, m), 7.42 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 369 (MH+). C23H29FN2O requires 368. Ret. time 1.99 min. The free base was dissolved in methanol. 1M HCl/diethylether was added to the stirred solution and stirring continued at room temperature for 5 minutes. The solution was then evaporated under reduced pressure, redissolved in DCM and evaporated at reduced pressure. The resulting foam was dried for 16 hours at reduced pressure. The hydrochloride salt was obtained as a white foam (1.45 g).

Quelle