4-chlorobutylsulfanylbenzene

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: 30% Aqueous hydrogen peroxide solution (27.6 ml) was dropwise added under ice-cooling to a solution of 4-phenylthiobutyl chloride (22.2 g) obtained in the same manner as in Preparation Example 99 in formic acid (150 ml), which was followed by stirring at room temperature for 1 hr. The reaction mixture was poured into ice water, neutralized with sodium hydroxide solution and extracted with chloroform. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform) and further recrystallized from hexane to give 21 g of 4-phenylsulfonylbutyl chloride. extracted with chloroform The organic layer was washed with brine dried the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography (chloroform) further recrystallized from hexane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11 g (0.1 mol) of thiophenol and 18.9 g (0.11 mol) of 1-bromo-4-chlorobutane are mixed at ordinary temperature in a 250 ml flask equipped with a condenser, a thermometer and a dropping funnel. 100 ml of ethanol are added, the mixture is heated to 40° C and 20 ml of 5N NaOH are then added dropwise at this temperature. The speed of addition of the sodium hydroxide is regulated so as to have a reaction medium of neutral pH. When the addition is complete, the reactants are left in contact at 40° C for 3 hours, the alcohol is then evaporated, the oil is extracted with ether and the ether solution is washed with 2N NaOH and then with water. Thereafter the organic phase is dried over MgSO4, the ether is evaporated and a yellow oil ia obtained, which crystallises from ethanol. (18.4 g; 0.092 mol; yield: about 92%). equipped with a condenser When the addition the alcohol is then evaporated the oil is extracted with ether the ether solution is washed with 2N NaOH Thereafter the organic phase is dried over MgSO4 the ether is evaporated a yellow oil ia obtained which crystallises from ethanol

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

Procedure: 30% Aqueous hydrogen peroxide solution (27.6 ml) was dropwise added under ice-cooling to a solution of 4-phenylthiobutyl chloride (22.2 g) obtained in the same manner as in Preparation Example 99 in formic acid (150 ml), which was followed by stirring at room temperature for 1 hr. The reaction mixture was poured into ice water, neutralized with sodium hydroxide solution and extracted with chloroform. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform) and further recrystallized from hexane to give 21 g of 4-phenylsulfonylbutyl chloride. extracted with chloroform The organic layer was washed with brine dried the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography (chloroform) further recrystallized from hexane

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: Prepared by Procedure R and Scheme Z using benzenethiol and 1-bromo-4-chlorobutane. Prepared by Procedure R and Scheme Z

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

Procedure: Prepared by Procedure G and Scheme B1 using [(4-chlorobutyl)sulfanyl]benzene and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 410.6 (M+H)+. Prepared by Procedure G and Scheme B1

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

Procedure: Prepared by Procedure G and Scheme B1 using [(4-chlorobutyl)sulfanyl]benzene and N-[3-(4-piperidinyl)phenyl]cyclopropanecarboxamide: ESMS m/e: 409.5 (M+H)+. Prepared by Procedure G and Scheme B1

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

Procedure: Prepared by Procedure G and Scheme B using [(4-chlorobutyl)sulfanyl]benzene and N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 396.8 (M+H)+. Prepared by Procedure G and Scheme B

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

Procedure: Prepared by Procedure R and Scheme Z using benzenethiol and 1-bromo-4-chlorobutane. Prepared by Procedure R and Scheme Z