3-Azabicyclo[3.2.2]nonane → 3-(5-Chloro-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

The title compound was prepared from the coupling of 3-azabicyclo[3.2.2]nonane and 5-chloro-2-naphthalenesulfonyl chloride. 3-Azabicyclo[3.2.2]nonane (0.31 g, 2.5 mmol) and diisopropyl ethyl amine (1.0 ml, 5.7 mmol) were dissolved in 10 ml chloroform. 5-Chloro-1-naphthalenesulfonyl chloride (0.50 g. 1.9 mmol) in 20 ml chloroform was added dropwise to the solution. After stirring overnight, the solution was washed with saturated sodium bicarbonate solution and brine. Drying over magnesium sulfate and evaporation followed by recrystallization with isopropyl ether/methanol gave 0.50 g (76% yield) of a yellow solid: mp 138°-139° C.; 1H NMR (CDCl3): 8.39 (d, J=8.9, 1 H, H3), 8.33 (d, J=1.7, 1 H, H1), 7.91-7.84 (m, 2 H, H4 and H6), 7.72 (d, J=7.5, 1 H, H8), 7.52 (t, J=7.9, 1 H, H7), 3.31 (d, J=4.2, 4 H, N (CH2R)2), 2.09 (s, 2 H, N(CH2CHR)2), 1.75-1.61 (m, 8 H, alkyl H's); anal calcd for C18H20 2 NO2SCl; C, 61.79; H, 5.76; N, 4.00; found: C, 61.89; H, 5.80; N. 4.08.

1. washthe solution was washed with saturated sodium bicarbonate solution and brine
2. dry with materialDrying over magnesium sulfate and evaporation
3. customfollowed by recrystallization with isopropyl ether/methanol

ORD record

ord-e870d6ab7355409991e31df3be5bb55b

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05707985