4-Bromo-2,5-difluoroanisole

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene, 1-(2-phenethyl)piperazine and ethyl acetate (extraction solvent) were replaced with 4-bromo-2,5-difluoroanisole (6.742 g), piperazine (12.404 g) and toluene (extraction solvent), respectively, to provide crude 1-(2,5-difluoro-4-methoxyphenyl)-piperazine (1.926 g).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 4-bromo-2,5-difluoroanisole (4.460 g) and ethyl isonipecotate (3.70 mL), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1) to provide ethyl 1-(2,5-difluoro-4-methoxyphenyl)piperidine-4-carboxylate (2.465 g). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 4-bromo-2,5-difluoroanisole (4.460 g) and ethyl isonipecotate (3.70 mL), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1) to provide ethyl 1-(2,5-difluoro-4-methoxyphenyl)piperidine-4-carboxylate (2.465 g). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=6:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-phenethylpiperazine were replaced with 4-bromo-2,5-difluoroanisole (1.115 g) and 1,4-dioxa-8-azaspiro[4,5]-decane (859 mg), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1) to provide 8-(2,5-difluoro-4-methoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decane (455 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-phenethylpiperazine were replaced with 4-bromo-2,5-difluoroanisole (1.115 g) and 1,4-dioxa-8-azaspiro[4,5]-decane (859 mg), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1) to provide 8-(2,5-difluoro-4-methoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decane (455 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 4-bromo-2,5-difluoroanisole (446 mg) and 4-(3-phenylpropyl)-piperidine (1.220 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=8:1) to provide 1-(2,5-difluoro-4-methoxyphenyl)-4-(3-phenylpropyl)piperidine (233 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=8:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-(2-phenethyl)piperazine were replaced with 4-bromo-2,5-difluoroanisole (446 mg) and 4-(3-phenylpropyl)-piperidine (1.220 g), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=8:1) to provide 1-(2,5-difluoro-4-methoxyphenyl)-4-(3-phenylpropyl)piperidine (233 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=8:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Production Example 9 was repeated except that 5-bromo-2-methoxytoluene and 1-phenethylpiperazine were replaced with 4-bromo-2,5-difluoroanisole (338 mg) and 4-(3-cyclohexylpropyl)-piperidine (953 mg), respectively. The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1) to provide 4-(3-cyclohexylpropyl)-1-(2,5-difluoro-4-methoxyphenyl)piperidine (523 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=3:1)