HCID 86059385, compound → HCID 58852350, compound

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Reaction Steps

Mix the above 1-(6-bromo-pyridin-2-yl)-4-dimethylamino-cyclohexanol (7 g, 23.4 mmol), p-toluenesulfonic acic monohydrate (15.3 g, 80.5 mmol), anhydrous toluene (600 mL). Heat at reflux for 16 hr. with a Dean Stark trap. Cool down to room temperature. Concentrate under reduced pressure. Partition between ethyl acetate and a 2M NaOH solution. Separate the organic layer, extract the aqueous layer twice with ethyl acetate. Combine the organic fractions, dry over sodium sulfate and concentrate to a residue. Purify the residue by chromatography (silica gel, 6% 2M NH3-MeOH in DCM) to yield (4-(6-bromo-pyridin-2-yl)-cyclohex-3-enyl)-dimethyl-amine (5.3 g, 81% yield): MS (ES): m/z=299 (M+H)+; 1H NMR (CDCl3): δ 7.45 (m, 1H), 7.27 (m, 2H), 6.72 (m, 1H), 2.69 (m, 1H), 2.45 (m, 3H), 2.33 (s, 6H), 2.21 (m, 2H), 1.58 (m, 1H).

Provenance & Evidence