Réaction #1902933

Équation de réaction

2-Chlorobenzothiazole

1,4-diazabicyclo[3.2.2]nonane

Et3N

→

title compound

Rendement 34.3%

4-BENZOTHIAZOL-2-YL-1,4-DIAZA-BICYCLO[3.2.2]NONANE

Rendement 34.3%

Solvants

EtOAc

H2O

DMF

Conditions de réaction

Traitement

1. 1
   Températureto cool to RT
2. 2
   Autrethe layers were partitioned
3. 3
   ExtractionThe aqueous layer was extracted with EtOAc (3×)
4. 4
   Lavagethe combined organic extracts were washed successively with H2O and brine
5. 5
   Séchagedried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude residue was purified by chromatography (Biotage, 12L)
9. 9
   Lavageeluting with 5% MeOH in CHCl3

Mode opératoire

2-Chlorobenzothiazole (Aldrich, 109 μL, 0.841 mmol) was added to a solution of 1,4-diazabicyclo[3.2.2]nonane (57%, 169 mg, 0.765 mmol), Et3N (213 μL, 1.53 mmol) in DMF (2.5 mL). The reaction mixture was heated at 100° C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc and H2O and the layers were partitioned. The aqueous layer was extracted with EtOAc (3×) and the combined organic extracts were washed successively with H2O and brine and then dried (Na2SO4), filtered and concentrated. The crude residue was purified by chromatography (Biotage, 12L) eluting with 5% MeOH in CHCl3 to afford 68 mg (34%) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 7.58 (d, 1H, J=7.9 Hz), 7.57 (d, 1H, J=7.9 Hz), 7.27 (t, 1H, J=8.3 Hz), 7.04 (td, 1H, J=7.9, 1.2 Hz), 4.31 (s, 1H), 3.92 (t, 2H, J=5.8 Hz), 3.19-2.98 (m, 6H), 2.25-2.16 (m, 2H), 1.84-1.77 (m, 2H), MS (Cl) m/z 260.2 (M+1). The hydrochloride salt was prepared by dissolving the title compound in iPrOH and adding 0.1 mL of 6 M hydrochloric acid.

Source