3-chloropropylbenzene

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:-7.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 84 mL of CH2Cl2 and 14.4 g (1.1 eq.) of aluminum trichloride (AlCl3) are placed in a reactor at 20° C. with stirring. The reaction medium is cooled to −7° C. and 8.5 g (1.1 eq.) of acetyl chloride are then added. The mixture is stirred for 30 minutes and 15 g of 1-chloro-3-phenylpropane are then added at 0° C. At the end of the reaction, the reaction mixture is poured over about 30 minutes with vigorous stirring into 75 mL of 5% hydrochloric acid solution. The mixture is stirred for 1 hour at 10° C., the phases are then separated by settling and the aqueous phase is extracted with CH2Cl2. The organic phases are combined and washed successively with 2N HCl solution, 1N sodium hydroxide solution and water. The mixture is stirred for 30 minutes At the end of the reaction the reaction mixture is poured over about 30 minutes The mixture is stirred for 1 hour at 10° C. the phases are then separated the aqueous phase is extracted with CH2Cl2 washed successively with 2N HCl solution, 1N sodium hydroxide solution and water

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

Procedure: 16.5 parts by weight of cyclohexene are added dropwise at +10° C. to a mixture of 31 parts by weight of 3-phenylpropyl chloride and 20 parts by weight of 96% strength sulfuric acid. Stirring is continued for 14 hours at room temperature. The crude product is dissolved in CHCl3 /ice water and the organic solution is thoroughly washed with ice water, dried over Na2CO3 and distilled. 27 parts by weight of 3-(4-cyclohexylphenyl)-propyl chloride are obtained; boiling point 126° C.-130° C./0.2 mm Hg, yield 57%(based on 3-phenylpropyl chloride). the organic solution is thoroughly washed with ice water dried over Na2CO3 distilled

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

Procedure: 16.5 parts by weight of cyclohexene are added dropwise at +10° C. to a mixture of 31 parts by weight of 3-phenylpropyl chloride and 20 parts by weight of 96% strength sulfuric acid. Stirring is continued for 14 hours at room temperature. The crude product is dissolved in CHCl3 /ice water and the organic solution is thoroughly washed with ice water, dried over Na2CO3 and distilled. 27 parts by weight of 3-(4-cyclohexylphenyl)-propyl chloride are obtained; boiling point 126° C.-130° C./0.2 mm Hg, yield 57%(based on 3-phenylpropyl chloride). the organic solution is thoroughly washed with ice water dried over Na2CO3 distilled

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

Procedure: Solid lithium hydroxide (anhydrous) (21.55 g, 0.9 mole, 0.9 equiv.) was added to a 3-neck Morton flask equipped with a mechanical stirrer, condenser, thermocouple and nitrogen. Solid (−)-cis-aminoindan-2-ol (3, 149.19 g, 1.0 mole) was then added, followed by dry THF (1.492 L, to give ˜100 g/l batch) at 20° C. The resulting slurry was stirred at 350 RPM. The KF of the solution was <1200 mg/l. 2-Methoxypropene (383.1 ml, 288.47 g, 4.0 mole, 4.0 equiv.) was then added subsurfacely. The flask was then placed in a 20° C. water bath, and neat hydrocinnamoyl chloride (2, 153.02 ml, 173.68 g, 1.03 mole, 1.03 equiv.) was added over 1.25 hours. At about 50% hydrocinnamoyl chloride addition, the solution became clear. At about 90% addition an exotherm occured (5-10° C.). Upon completion of the addition of 2 the batch was warmed to 40° C. and aged until >99.0% conversion (as measured by HPLC assay) to acetonide 1 was achieved. Additional lithium hydroxide (5.99 g, 0.25 mole, 0.25 eq.) was added to the batch to quench excess HCl by-product. The batch was stirred for one hour. Upon quench the batch turned from clear to golden in appearance. Residual HCl was determined by titration to be less than 0.005 mmol. The solution yield was 98%. equipped with a mechanical stirrer, condenser was then placed in a 20° C. At about 90% addition an exotherm (5-10° C.) Upon completion of the addition of 2 the batch to quench excess HCl by-product The batch was stirred for one hour Upon quench the batch

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

Procedure: Solid lithium hydroxide (anhydrous) (21.55 g, 0.9 mole, 0.9 equiv.) was added to a 3-neck Morton flask equipped with a mechanical stirrer, condenser, thermocouple and nitrogen. Solid (−)-cis-aminoindan-2-ol (3, 149.19 g, 1.0 mole) was then added, followed by dry THF (1.492 L, to give ˜100 g/l batch) at 20° C. The resulting slurry was stirred at 350 RPM. The KF of the solution was <1200 mg/l. 2-Methoxypropene (383.1 ml, 288.47 g, 4.0 mole, 4.0 equiv.) was then added subsurfacely. The flask was then placed in a 20° C. water bath, and neat hydrocinnamoyl chloride (2, 153.02 ml, 173.68 g, 1.03 mole, 1.03 equiv.) was added over 1.25 hours. At about 50% hydrocinnamoyl chloride addition, the solution became clear. At about 90% addition an exotherm occured (5-10° C.). Upon completion of the addition of 2 the batch was warmed to 40° C. and aged until >99.0% conversion (as measured by HPLC assay) to acetonide 1 was achieved. Additional lithium hydroxide (5.99 g, 0.25 mole, 0.25 eq.) was added to the batch to quench excess HCl by-product. The batch was stirred for one hour. Upon quench the batch turned from clear to golden in appearance. Residual HCl was determined by titration to be less than 0.005 mmol. The solution yield was 98%. equipped with a mechanical stirrer, condenser was then placed in a 20° C. At about 90% addition an exotherm (5-10° C.) Upon completion of the addition of 2 the batch to quench excess HCl by-product The batch was stirred for one hour Upon quench the batch

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.15 mole of 1-methylimidazole and 0.125 mole of 1-chloro-3-phenylpropane were introduced into a 100 mL round bottom flask and stirred at 70° C. for one day to obtain 1-(3-phenylpropyl)-3-methylimidazolium chloride (yield 99%).

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.15 mole of 1-methylimidazole and 0.125 mole of 1-chloro-3-phenylpropane were introduced into a 100 mL round bottom flask and stirred at 70° C. for one day to obtain 1-(3-phenylpropyl)-3-methylimidazolium chloride (yield 99%).

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

Procedure: The titled compound (44 mg) as a white solid was prepared from the compound [4-6] obtained in the process (6) of Example 4 (100 mg) and 3-phenylpropyl chloride according to the method of the process (7) of Example 4.

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

Procedure: The titled compound (44 mg) as a white solid was prepared from the compound [4-6] obtained in the process (6) of Example 4 (100 mg) and 3-phenylpropyl chloride according to the method of the process (7) of Example 4.