1-(3-Bromo-2-fluoro-phenyl)-4-dimethylamino-cyclohexanol → (4-(3-Bromo-2-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine
Reaction equation
[Br:1][C:2]1[C:3]([F:18])=[C:4]([C:8]2(O)[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([F:18])=[C:4]([C:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[CH3:16])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Heat 1-(3-bromo-2-fluoro-phenyl)-4-dimethylamino-cyclohexanol (preparation 6, 2.04 g, 6.45 mmol) and p-TsOH monohydrate (3.07 g, 16 mmol) in toluene (50 mL) at reflux for 2 hr. Partition the reaction mixture between saturated aqueous NaCl and ethyl acetate, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and purify the residue by chromatography on a silica gel column (DCM: 2M NH3 in MeOH, gradient) to give the title product (1.70 g): MS (ES): m/z=300 (M+H)+ and 298 (M−H)−. 1HNMR (CDCl3): δ 7.39 (m, 1H), 7.14 (m, 1H), 6.94 (m, 1H), 5.88 (m, 1H), 2.60-2.38 (m, 4H), 2.35 (s, 6H), 2.20 (m, 1H), 2.08 (m, 1H), 1.56 (m, 1H).