Sodium Bicarbonate → 3-(6-Chloro-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane dihydrochloride

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Reaction Steps

The product from Example 11A (0.03 g; 0.103 mmol) in 12M HCl (0.13 mL) was treated with sodium nitrite (10 mg, 0.129 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stir overnight. The mixture was neutralized by addition of NaHCO3 and then extracted with CH2Cl2. The extracts were dried (Na2SO4), concentrated under reduced pressure, and the residue purified on SiO2 (10% MeOH/CH2Cl2/1% NH4OH) to provide the free base. The free base was treated with 1M HCl/ether to provide the title compound (43% yield). 1H NMR free base (CDCl3, 300 MHz) δ 1.8 (m, 4H), 2.1 (br s, 1H, exchangeable), 3.0 (d.K=11 Hz, 2H), 3.4-3.7 (br s, 2H), 7.0-7.2 (m, 2H0, 7.9 (m, 1H).

Provenance & Evidence