1-[(4-bromophenyl)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:

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

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

Procedure: 4-Bromobenzylbromide (3 g) was stirred with 4-hydroxypiperidine (1.21 g) and potassium carbonate (1.99 g) in dimethylacetamide (15 ml) at 50° C. for 3 h The reaction mixture was then allowed to cool, poured into water (80 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography, eluting with a gradient of 0-3% methanol in dichloromethane, to afford the product as a viscous, colourless oil (2.02 g). to cool extracted with ethyl acetate (3×50 ml) The combined extracts were washed with water dried (MgSO4) filtered evaporated The residue was purified by column chromatography eluting with a gradient of 0-3% methanol in dichloromethane

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

Procedure: 4-Bromobenzylbromide (3 g) was stirred with 4-hydroxypiperidine (1.21 g) and potassium carbonate (1.99 g) in dimethylacetamide (15 ml) at 50° C. for 3 h The reaction mixture was then allowed to cool, poured into water (80 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography, eluting with a gradient of 0-3% methanol in dichloromethane, to afford the product as a viscous, colourless oil (2.02 g). to cool extracted with ethyl acetate (3×50 ml) The combined extracts were washed with water dried (MgSO4) filtered evaporated The residue was purified by column chromatography eluting with a gradient of 0-3% methanol in dichloromethane

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

Procedure: 0.428 g (0.00184 mol) of 1-(4-bromo-benzyl)-piperidin-4-ol was dissolved in 8 ml of dimethylformamide and treated with 0.097 g (0.00079 mol) of dimethylaminopyridine and 0.222 g (0.00158 mol) of 4-fluoro-benzoic acid. The mixture was cooled to 0° and 0.334 g (0.00174 mol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added. The mixture was warmed to room temperature and stirred for 18 hrs. The solvent was distilled off and the residue was taken up in ethyl acetate and treated with silica gel. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent. 0.47 g (76%) of 1-(4-bromo-benzyl)-piperidin-4-yl 4-fluoro-benzoate was obtained as a colorless oil. The mixture was cooled to 0° The solvent was distilled off treated with silica gel After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent

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

Procedure: 0.27 g (0.001 mol) of 1-(4-bromo-benzyl)-piperidin-4-ol and 0.359 ml (0.0025 mol) of triethylamine were dissolved in 10 ml of toluene, treated with 0.16 ml (0.00125 mol) of 4-chlorobenzoyl 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). 0.333 g (81.5%) of 1-(4-bromo-benzyl)-piperidin-4-yl 4-chloro-benzoate was obtained as a colorless oil. 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: 0.108 g (0.0004 mol) of 1-(4-bromo-benzyl)-piperidin-4-ol and 0.12 ml (0.00085 mol) of triethylamine were dissolved in 4 ml of toluene, treated with 0.058 ml (0.0005 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 (1:1). 0.125 g (83.5%) of 1-(4-bromo-benzyl)-piperidin-4-yl benzoate was obtained as a colorless oil. at reflux for 18 hrs The reaction mixture was concentrated the residue was chromatographed over silica gel with ethyl acetate/hexane (1:1)

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

Procedure: 0.202 g (0.002 mol) of 4-hydroxypiperidine and 0.55 g (0.0022 mol) of 4-bromobenzyl bromide were dissolved in 5 ml of dimethylformamide and stirred at room temperature for 2 hrs. The solvent was distilled off and the residue was taken up in dichloromethane and washed with sat. bicarbonate solution and sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated. 0.54 g (100%) of 1-(4-bromo-benzyl)-piperidin-4-ol was obtained as a colorless oil. MS: me/e (% basic peak)=271, 269 (C12H16BrNO30 , 73, 76), 270, 268 (79, 70), 171, 169 (99, 100), 114 (64), 100 (60). The solvent was distilled off washed with sat. bicarbonate solution and sodium chloride solution The organic phase was dried over sodium sulfate concentrated

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

Procedure: 4-Bromobenzylbromide (3 g) was stirred with 4-hydroxypiperidine (1.21 g) and potassium carbonate (1.99 g) in dimethylacetamide (15 ml) at 50° C. for 3 h. The reaction mixture was then allowed to cool, poured into water (80 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography, eluting with a gradient of 0–3% methanol in dichloromethane, to afford the product as a viscous, colourless oil (2.02 g). to cool extracted with ethyl acetate (3×50 ml) The combined extracts were washed with water dried (MgSO4) filtered evaporated The residue was purified by column chromatography eluting with a gradient of 0–3% methanol in dichloromethane