4-(2-piperidin-1-ylethyl)aniline

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: In ethanol (100 ml) was dissolved 1-[2-(4-nitrophenyl)ethyl]piperidine (24.8 g), and to the mixture was added dried 10% palladium on carbon (1.24 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 86 hours. The palladium was filtered off, and the filtrate was concentrated to give 1-[2-(4-aminophenyl)ethyl]-piperidine (21.7 g) as pale brown oil. to the mixture was added dried 10% palladium on carbon (1.24 g) The palladium was filtered off the filtrate was concentrated

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

Procedure: In ethanol (100 ml) was dissolved 1-[2-(4-nitrophenyl)ethyl]piperidine (24.8 g), and to the mixture was added dried 10% palladium on carbon (1.24 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 86 hours. The palladium was filtered off, and the filtrate was concentrated to give 1-[2-(4-aminophenyl)ethyl]-piperidine (21.7 g) as pale brown oil. to the mixture was added dried 10% palladium on carbon (1.24 g) The palladium was filtered off the filtrate was concentrated

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

Procedure: Prepared analogously to Example 82 from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-nitro-2-indolinone and 4-(2-piperidinoethyl)-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol.

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-[2-(4-Nitro-phenyl)-ethyl]-piperidine (0.1178 gms.) is suspended in 4.5 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then immersed in a 65° C. oil bath and treated in dropwise fashion with 9 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is maintained in the 65° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to 0° C., and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is then extracted with chloroform. The emmulsion that forms is filtered through glass wool, re-extracted with chloroform, and then dried over anhydrous sodium sulfate. Following evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform) to yield 60 mg of 4-(2-piperidin-1-yl-ethyl)-phenylamine. is then immersed in a 65° C. Over the course of the addition a color change from colorless to purple to black ensues The reaction mixture is then cooled to 0° C. The basic reaction mixture is then extracted with chloroform The emmulsion that forms is filtered through glass wool re-extracted with chloroform dried over anhydrous sodium sulfate evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform)

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

Procedure: Prepared analogously to Example 82 from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-nitro-2-indolinone and 4-(2-piperidinoethyl)-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol.

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-[2-(4-Nitro-phenyl)-ethyl]-piperidine (0.1178 gms.) is suspended in 4.5 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then immersed in a 65° C. oil bath and treated in dropwise fashion with 9 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is maintained in the 65° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to 0° C., and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is then extracted with chloroform. The emmulsion that forms is filtered through glass wool, re-extracted with chloroform, and then dried over anhydrous sodium sulfate. Following evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform) to yield 60 mg of 4-(2-piperidin-1-yl-ethyl)-phenylamine. is then immersed in a 65° C. Over the course of the addition a color change from colorless to purple to black ensues The reaction mixture is then cooled to 0° C. The basic reaction mixture is then extracted with chloroform The emmulsion that forms is filtered through glass wool re-extracted with chloroform dried over anhydrous sodium sulfate evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform)

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

Procedure: In ethanol (100 ml) was dissolved 1-[2—(4-nitro-phenyl)ethyl]piperidine (24.8g), and to the mixture was added dried 10% palladium on carbon (1.24 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 86 hours. The palladium was filtered off, and the filtrate was concentrated to give 1-[2—(4-aminophenyl)ethyl]-piperidine (21.7 g) as pale brown oil. to the mixture was added dried 10% palladium on carbon (1.24 g) The palladium was filtered off the filtrate was concentrated

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-[2-(4-Nitro-phenyl)-ethyl]-piperidine (0.1178 gms.) is suspended in 4.5 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then immersed in a 65° C. oil bath and treated in dropwise fashion with 9 mL of an ˜10 wt. % solution of TiCl3 in 20-30 wt. % HCl. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is maintained in the 65° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to 0° C., and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is then extracted with chloroform. The emulsion that forms is filtered through glass wool, re-extracted with chloroform, and then dried over anhydrous sodium sulfate. Following evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform) to yield 60 mg of 4-(2-piperidin-1-yl-ethyl)-phenylamine. is then immersed in a 65° C. Over the course of the addition a color change from colorless to purple to black ensues The reaction mixture is then cooled to 0° C. The basic reaction mixture is then extracted with chloroform The emulsion that forms is filtered through glass wool re-extracted with chloroform dried over anhydrous sodium sulfate evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-[2-(4-Nitro-phenyl)-ethyl]-piperidine (0.1178 gms.) is suspended in 4.5 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then immersed in a 65° C. oil bath and treated in dropwise fashion with 9 mL of an 10 wt. % solution of TiCl3 in 20-30 wt. % HCl. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is maintained in the 65° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to 0° C., and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is then extracted with chloroform. The emmulsion that forms is filtered through glass wool, re-extracted with chloroform, and then dried over anhydrous sodium sulfate. Following evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform) to yield 60 mg of 4-(2-piperidin-1-yl-ethyl)-phenylamine. is then immersed in a 65° C. Over the course of the addition a color change from colorless to purple to black ensues The reaction mixture is then cooled to 0° C. The basic reaction mixture is then extracted with chloroform The emmulsion that forms is filtered through glass wool re-extracted with chloroform dried over anhydrous sodium sulfate evaporation of the solvent the residue is chromatographed by flash silica gel chromatography (10% methanol in chloroform)