4-BENZYLOXY-3-FLUORO-BROMOBENZENE

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:

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

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

Procedure: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (6.742 g) and piperazine (12.404 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1) to provide 1-(4-benzyloxy-3-fluorophenyl)piperazine (3.716 g). The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1)

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

Procedure: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (6.742 g) and piperazine (12.404 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1) to provide 1-(4-benzyloxy-3-fluorophenyl)piperazine (3.716 g). The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1)

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

Procedure: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenylethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (1.42 g) and 1-(3-cyclo-hexylpropyl)piperazine (1.28 g), respectively, to provide crude 1-(4-benzyloxy-3-fluorophenyl)-4-(3-cyclohexylpropyl)piperazine (2.31 g).

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

Procedure: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenylethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (1.42 g) and 1-(3-cyclo-hexylpropyl)piperazine (1.28 g), respectively, to provide crude 1-(4-benzyloxy-3-fluorophenyl)-4-(3-cyclohexylpropyl)piperazine (2.31 g).

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

Procedure: A reaction vessel was charged with 19.4 g of 2-fluoro-4-bromophenol, 12.9 g of benzyl chloride, 23.3 g of potassium carbonate and 510 ml of cyclohexanone and the reaction was carried out with stirring at 120°-140° C. for 7 hours. The reaction liquid was poured into dilute hydrochloric acid and then extracted with benzene. The benzene layer was washed with water and dried over Glauber's salt. The benzene was distilled off and the residue was purified by way of column chromatography on silica gel (eluent: hexane/benzene=4/1) to obtain 27.9 g (yield 97.3%) of 2-fluoro-4-bromophenyl benzyl ether. The reaction liquid extracted with benzene The benzene layer was washed with water dried over Glauber's salt The benzene was distilled off the residue was purified by way of column chromatography on silica gel (eluent: hexane/benzene=4/1)

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

Procedure: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 1-benzyloxy-4-bromo-2-fluorobenzene (6.742 g) and piperazine (12.404 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1) to provide 1-(4-benzyloxy-3-fluorophenyl)piperazine (3.716 g). The resulting crude product was purified on silica gel column chromatography (eluent, chloroform: methanol=2:1)