4-(2-hydroxyphenyl)piperidin-4-ol

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 20 mL of anhydrous dimethylformamide were dissolved 3.5 g (10 mmol) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide and 1.93 g (10 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 3.2 g (30 mmol) of sodium carbonate, followed by stirring at 80° C. for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with water and dried. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 3.6 g (yield: 78.6%) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 1) was obtained. The reaction mixture was distilled under reduced pressure to remove the solvent the residue thus obtained The resulting solution was washed with water dried The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 20 mL of anhydrous dimethylformamide were dissolved 3.5 g (10 mmol) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide and 1.93 g (10 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 3.2 g (30 mmol) of sodium carbonate, followed by stirring at 80° C. for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with water and dried. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 3.6 g (yield: 78.6%) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 1) was obtained. The reaction mixture was distilled under reduced pressure to remove the solvent the residue thus obtained The resulting solution was washed with water dried The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 50 mL of anhydrous dimethylformamide were dissolved 2.24 g (6.7 mmol) of methyl 4-bromo-2,2-diphenylbutyrate and 1.30 g (6.7 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 1.07 g (10 mmol) of sodium carbonate, followed by stirring under heating at 50° C. for 35 hours. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate, followed by washing with water and drying. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 870 mg (yield: 29.2%) of methyl 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-2,2-diphenylbutyrate was obtained. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate by washing with water drying The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 50 mL of anhydrous dimethylformamide were dissolved 2.24 g (6.7 mmol) of methyl 4-bromo-2,2-diphenylbutyrate and 1.30 g (6.7 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 1.07 g (10 mmol) of sodium carbonate, followed by stirring under heating at 50° C. for 35 hours. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate, followed by washing with water and drying. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 870 mg (yield: 29.2%) of methyl 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-2,2-diphenylbutyrate was obtained. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate by washing with water drying The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

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

Procedure: In 100 mL of methanol was dissolved 12 g (32 mmol) of 1-benzyl-4-(2-benzyloxyphenyl)-4-piperidinol. To the resulting solution was added 3 g of 20% palladium hydroxide carbon and the resulting mixture was subjected to catalytic reduction at room temperature for 6 hours under 4 atmospheric pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure, whereby 6.7 g (yield: 100%) of 4-(2-hydroxyphenyl)-4-piperidinol was obtained. After completion of the reaction the catalyst was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: In 100 mL of methanol was dissolved 12 g (32 mmol) of 1-benzyl-4-(2-benzyloxyphenyl)-4-piperidinol. To the resulting solution was added 3 g of 20% palladium hydroxide carbon and the resulting mixture was subjected to catalytic reduction at room temperature for 6 hours under 4 atmospheric pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure, whereby 6.7 g (yield: 100%) of 4-(2-hydroxyphenyl)-4-piperidinol was obtained. After completion of the reaction the catalyst was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 20 mL of anhydrous dimethylformamide were dissolved 3.5 g (10 mmol) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide and 1.93 g (10 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 3.2 g (30 mmol) of sodium carbonate, followed by stirring at 80° C. for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with water and dried. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 3.6 g (yield: 78.6%) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 1) was obtained. The reaction mixture was distilled under reduced pressure to remove the solvent the residue thus obtained The resulting solution was washed with water dried The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 50 mL of anhydrous dimethylformamide were dissolved 2.24 g (6.7 mmol) of methyl 4-bromo-2,2-diphenylbutyrate and 1.30 g (6.7 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 1.07 g (10 mmol) of sodium carbonate, followed by stirring under heating at 50° C. for 35 hours. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate, followed by washing with water and drying. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 870 mg (yield: 29.2%) of methyl 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-2,2-diphenylbutyrate was obtained. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate by washing with water drying The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column

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

Procedure: In 100 mL of methanol was dissolved 12 g (32 mmol) of 1-benzyl-4-(2-benzyloxyphenyl)-4-piperidinol. To the resulting solution was added 3 g of 20% palladium hydroxide carbon and the resulting mixture was subjected to catalytic reduction at room temperature for 6 hours under 4 atmospheric pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure, whereby 6.7 g (yield: 100%) of 4-(2-hydroxyphenyl)-4-piperidinol was obtained. After completion of the reaction the catalyst was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 20 mL of anhydrous dimethylformamide were dissolved 3.5 g (10 mmol) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide and 1.93 g (10 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 3.2 g (30 mmol) of sodium carbonate, followed by stirring at 80° C. for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with water and dried. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 3.6 g (yield: 78.6%) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 1) was obtained. The reaction mixture was distilled under reduced pressure to remove the solvent the residue thus obtained The resulting solution was washed with water dried The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column