3-Chlorobenzoic Acid → 3-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-OL 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:16])[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=C(C=CC=1)C(O)=[O:22]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:16])[CH2:13][CH2:12][N+:11]([O-:22])([CH2:14][CH3:15])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(3-chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol (0.65 g, 2.67 mmol) was dissolved in dichloromethane (30 ml) and m-chlorobenzoic acid (1.38 g, 8.01 mmol) was added in portions. The mixture was stirred at ambient temperature for 15 h after which about 75% of the solvent was evaporated. The resulting slurry was purified with flash chromatography on basic Al2O3 eluted with methanol. The methanol was evaporated and dichloromethane (50 ml) and aqueous sodium carbonate (10%, 50 mL) was added. The organic phase was dried (MgSO4) and evaporated to give the title compound (0.45 g). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 158-160° C.