1-[(4-fluorophenyl)methyl]piperidin-4-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.5 g (0.00239 mol) of 1-(4-fluoro-benzyl)-piperidin-4-ol and 0.67 ml (0.00478 mol) of triethylamine were dissolved in 15 ml of toluene, treated with 0.632 ml (0.00478 mol) of p-toluoyl chloride and boiled at reflux for 18 hrs. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:2). 0.355 g (59%) of 1-(4-fluoro-benzyl)-piperidin-4-yl 4-methyl-benzoate was obtained as a yellow oil. MS: me/e=328 (C2H23FNO2+). at reflux for 18 hrs The reaction mixture was concentrated the residue was chromatographed over silica gel with ethyl acetate/hexane (1:2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.63 g (0.003 mol) of 1-(4-fluoro-benzyl)-piperidin-4-ol and 2.09 ml (0.015 mol) of triethylamine were dissolved in 30 ml of toluene, treated with 1.04 ml (0.009 mol) of benzoyl chloride and boiled at reflux for 18 hrs. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:3). 0.415 g (44%) of 1-(4-fluoro-benzyl)-piperidin-4-yl benzoate was obtained as a yellow oil. MS: me/e=314 (C19H21FNO2+). at reflux for 18 hrs The reaction mixture was concentrated the residue was chromatographed over silica gel with ethyl acetate/hexane (1:3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.856 g (0.00846 mol) of 4-hydroxypiperidine was dissolved in 40 ml of dimethylformamide and cooled to 0°. 2.0 g (0.0106 mol) of 4-fluorobenzyl bromide and 3.3 ml (0.0233 mol) of triethylamine were added under argon and the mixture was left to come to room temperature. It was stirred for 16 hrs., the solvent was distilled off and the residue was chromatographed on silica gel with dichloromethane/methanol (17:3) as the eluent. An analytically pure sample was obtained after a second chromatography on silica gel with dichloromethane/methanol (17:3) as the eluent. The remainder was used directly in the next step. 0.176 g (8%) of 1-(4-fluoro-benzyl-piperidin-4-ol was obtained as a yellow oil. MS: me/e=210 (C12H17FNO+). cooled to 0° the mixture was left to come to room temperature , the solvent was distilled off the residue was chromatographed on silica gel with dichloromethane/methanol (17:3) as the eluent An analytically pure sample was obtained after a second chromatography on silica gel with dichloromethane/methanol (17:3) as the eluent