Sodium Carbonate → 4-Chloro-10-azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene hydrochloride

1-(4-Chloro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (470 mg, 1.62 mmol) and Na2CO3 (344 mg, 3.24 mmol) in methanol (30 mL) and H2O (10 mL) were heated to reflux. After 2 hours, the reaction was cooled and diluted with water then extracted with ethyl acetate (4×40 mL), dried (Na2SO4), filtered and concentrated to a yellow oil. The crude material was treated with excess 3N HCl ethyl acetate and concentrated, then dissolved in a minimum of CH2Cl2 and the solution was saturated with hexanes and stirred. After stirring 4 hours the product was collected by filtration (155 mg, 42%). 1H NMR (free base) (400 MHz, CDCl3) δ 7.15 (m, 2H), 7.09 (d, J=8.0 Hz, 1H), 3.00–2.94 (m, 4H), 2.68, (m, 2H), 2.38 (m, 1H), 1.92 (d, J=10.5 Hz, 1H). 1H NMR (HCl salt) (400 MHz, DMSO-d6) δ 7.30–7.20 (m, 3H), 3.30–3.15 (m, 6H), 2.37 (m, 1H), 1.89 (d, J=11.0 Hz, 1H). APCI MS m/e 194.1 [(M+1)+].

1. temperaturethe reaction was cooled
2. extractionthen extracted with ethyl acetate (4×40 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated to a yellow oil
6. additionThe crude material was treated with excess 3N HCl ethyl acetate
7. concentrationconcentrated
8. dissolutiondissolved in a minimum of CH2Cl2
9. stirringAfter stirring 4 hours the product
10. filtrationwas collected by filtration (155 mg, 42%)

ORD record

ord-838100bfc1eb4170bffb41fdeff481cd

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091372B2