4-(2-chloroethyl)phenol

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

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

Procedure: In a similar process using 12N HCl, 2-(4-hydroxyphenyl) ethanol gave 70% isolated yield of the (2-[4-hydroxyphenyl]ethyl) chloride. 1H NMR (CDCl3) δ 2.96 (2H, t, J=7.8 Hz), 3.67 (2H, t, J=7.2 Hz), 6.79 (2H, d, J=8.4 Hz), 6.94 (2H, d, J=8.1 Hz) gave 70%

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

Procedure: In a similar process using 12N HCl, 2-(4-hydroxyphenyl) ethanol gave 70% isolated yield of the (2-[4-hydroxyphenyl]ethyl) chloride. 1H NMR (CDCl3) δ 2.96 (2H, t, J=7.8 Hz), 3.67 (2H, t, J=7.2 Hz), 6.79 (2H, d, J=8.4 Hz), 6.94 (2H, d, J=8.1 Hz) gave 70%

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

Procedure: The procedure described in Example 1 was repeated except that 4-(3-trifluoromethylphenyl)piperidine (the product of Preparation L) and 2-(p-hydroxyphenyl)ethyl chloride were the respective starting materials employed, using the same molar porportions as before. In this particular case, the corresponding final product obtained 4-{2-[4-(3-trifluoromethylphenyl)-piperidinyl]ethyl}phenol (yield, 65%), which was also converted to the hydrochloride salt. The pure base product was characterized by means of nuclear magnetic resonance data: NMR (CDCl3) δ6.8-7.6 (m, 8H), 0.6-4.0 (m, 14H). The hydrochloride salt melted at 207°-210° C. and was further characterized by means of elemental analysis.

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

Procedure: The procedure described in Example 1 was repeated except that 4-(3-trifluoromethylphenyl)piperidine (the product of Preparation L) and 2-(p-hydroxyphenyl)ethyl chloride were the respective starting materials employed, using the same molar porportions as before. In this particular case, the corresponding final product obtained 4-{2-[4-(3-trifluoromethylphenyl)-piperidinyl]ethyl}phenol (yield, 65%), which was also converted to the hydrochloride salt. The pure base product was characterized by means of nuclear magnetic resonance data: NMR (CDCl3) δ6.8-7.6 (m, 8H), 0.6-4.0 (m, 14H). The hydrochloride salt melted at 207°-210° C. and was further characterized by means of elemental analysis.

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

Procedure: A solution of concentrated nitric acid (1.8 ml) in acetic acid (4 ml) was added to a stirred solution of 4-hydroxyphenethyl chloride (4.5 g) in acetic acid (25 ml), keeping the temperature below 15°. The mixture was then stirred at 10° for 3.5 hours, poured into water, and extracted into ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (50 g) using hexane plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (3.2 g, 55%), m.p. 53°-55°. the temperature below 15° extracted into ethyl acetate The organic extract was washed with 5% aqueous sodium carbonate solution dried over magnesium sulphate evaporated The residue was purified by chromatography on silica (50 g) evaporated

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

Procedure: A solution of concentrated nitric acid (1.8 ml) in acetic acid (4 ml) was added to a stirred solution of 4-hydroxyphenethyl chloride (4.5 g) in acetic acid (25 ml), keeping the temperature below 15°. The mixture was then stirred at 10° for 3.5 hours, poured into water, and extracted into ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (50 g) using hexane plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (3.2 g, 55%), m.p. 53°-55°. the temperature below 15° extracted into ethyl acetate The organic extract was washed with 5% aqueous sodium carbonate solution dried over magnesium sulphate evaporated The residue was purified by chromatography on silica (50 g) evaporated

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

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

Procedure: A solution of concentrated nitric acid (1.8 ml) in acetic acid (4 ml) was added to a stirred solution of 4-hydroxyphenethyl chloride (4.5 g) in acetic acid (25 ml), keeping the temperature below 15°. The mixture was then stirred at 10° for 3.5 hours, poured into water, and extracted into ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (50 g) using hexane plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (3.2 g, 55%), m.p. 53°-55°. the temperature below 15° extracted into ethyl acetate The organic extract was washed with 5% aqueous sodium carbonate solution dried over magnesium sulphate evaporated The residue was purified by chromatography on silica (50 g) evaporated

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

Procedure: In a similar process using 12N HCl, 2-(4-hydroxyphenyl) ethanol gave 70% isolated yield of the (2-[4-hydroxyphenyl]ethyl) chloride. 1H NMR (CDCl3) δ 2.96 (2H, t, J=7.8 Hz), 3.67 (2H, t, J=7.2 Hz), 6.79 (2H, d, J=8.4 Hz), 6.94 (2H, d, J=8.1 Hz) gave 70%

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

Procedure: The procedure described in Example 1 was repeated except that 4-(3-trifluoromethylphenyl)piperidine (the product of Preparation L) and 2-(p-hydroxyphenyl)ethyl chloride were the respective starting materials employed, using the same molar porportions as before. In this particular case, the corresponding final product obtained 4-{2-[4-(3-trifluoromethylphenyl)-piperidinyl]ethyl}phenol (yield, 65%), which was also converted to the hydrochloride salt. The pure base product was characterized by means of nuclear magnetic resonance data: NMR (CDCl3) δ6.8-7.6 (m, 8H), 0.6-4.0 (m, 14H). The hydrochloride salt melted at 207°-210° C. and was further characterized by means of elemental analysis.

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

Procedure: A solution of concentrated nitric acid (1.8 ml) in acetic acid (4 ml) was added to a stirred solution of 4-hydroxyphenethyl chloride (4.5 g) in acetic acid (25 ml), keeping the temperature below 15°. The mixture was then stirred at 10° for 3.5 hours, poured into water, and extracted into ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (50 g) using hexane plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (3.2 g, 55%), m.p. 53°-55°. the temperature below 15° extracted into ethyl acetate The organic extract was washed with 5% aqueous sodium carbonate solution dried over magnesium sulphate evaporated The residue was purified by chromatography on silica (50 g) evaporated