N-[(2-aminophenyl)methyl]-1-benzylpiperidin-4-amine

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: Then, 590 mg of 1-benzyl-4-[N-(o-aminobenzyl)amino]-piperidine, 600 mg of sulfurylamide and 12 ml of pyridine are mixed and refluxed with heating for 2 hours. The reaction mixture is cooled to room temperature and poured into 50 ml of ice water. The white crystals deposited are separated by filtration, washed with 10 ml of water and dried to obtain 520 mg of the desired product as crystals. refluxed with heating for 2 hours The white crystals deposited are separated by filtration washed with 10 ml of water dried

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

Procedure: In this reference example, 1.10 g of 1-benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride is mixed with 5 ml of water. Then, 15 ml of 1 N aqueous sodium hydroxide is added to the solution with cooling. The mixture is extracted with 20 ml of chloroform four times. The chloroform layer is washed with 20 ml of water two times. The resultant layer is dried and concentrated under reduced pressure to obtain 670 mg of 1-benzyl-4-[N-(o-aminobenzyl)amino]-piperidine as an oily residue. with cooling The mixture is extracted with 20 ml of chloroform four times The chloroform layer is washed with 20 ml of water two times The resultant layer is dried concentrated under reduced pressure

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: Then, 590 mg of 1-benzyl-4-[N-(o-aminobenzyl)amino]-piperidine, 600 mg of sulfurylamide and 12 ml of pyridine are mixed and refluxed with heating for 2 hours. The reaction mixture is cooled to room temperature and poured into 50 ml of ice water. The white crystals deposited are separated by filtration, washed with 10 ml of water and dried to obtain 520 mg of the desired product as crystals. refluxed with heating for 2 hours The white crystals deposited are separated by filtration washed with 10 ml of water dried

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

Procedure: In this reference example, 1.10 g of 1-benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride is mixed with 5 ml of water. Then, 15 ml of 1 N aqueous sodium hydroxide is added to the solution with cooling. The mixture is extracted with 20 ml of chloroform four times. The chloroform layer is washed with 20 ml of water two times. The resultant layer is dried and concentrated under reduced pressure to obtain 670 mg of 1-benzyl-4-[N-(o-aminobenzyl)amino]-piperidine as an oily residue. with cooling The mixture is extracted with 20 ml of chloroform four times The chloroform layer is washed with 20 ml of water two times The resultant layer is dried concentrated under reduced pressure

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

Procedure: A solution of (2-amino-benzyl)-(1-benzyl-piperidin-4-yl)-amine (1.0 g, 3.39 mmol) and sulfamide (0.64 g, 6.78 mmol) in pyridine was heated at reflux for 14 h. After cooling to room temperature, the solvent was evaporated and the crude product dissolved in water. After being adjusted to pH 9 with 6N sodium hydroxide, the resulting mixture was extracted with methylene chloride (2×). The extracts were washed with water (2×), dried over sodium sulfate, filtered, and concentrated to afford an oily residue which was dissolved in ethyl acetate (4 mL). This solution was mixed with 4N HCl in 1,4-dioxane (2 mL) followed by addition of diethyl ether until precipitation of product occurred. The desired product was obtained by filtration to afford 0.7 g (53%). LC/MS: tR=0.96 min, 358.16 (MH)+. at reflux for 14 h the solvent was evaporated the crude product dissolved in water the resulting mixture was extracted with methylene chloride (2×) The extracts were washed with water (2×) dried over sodium sulfate filtered concentrated to afford an oily residue which

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1-Benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine (1.2 g, 3.7 mmol) and zinc dust (1 g, excess) were combined in 75% aqueous acetic acid (16 mL) and stirred at 60° C. for 2 h. After cooling to room temperature, the solvents were removed in vacuo and the resultant crude dissolved in water (10 mL), followed by addition of ammonium hydroxide until pH 3 was attained. The solution was extracted with methylene chloride (3×). The organic layers were pooled together washed with water (2×), brine (2×), dried over sodium sulfate, filtered, and concentrated to afford 0.8 g (73%) of the desired product. 1H-NMR (CD3OD) δ 2.50 (m, 2H), 3.20 (m, 2H), 3.49 (dd, J=7.0, 7.3, 1H), 3.62 (m, 4H), 4.20 (s, 2H), 4.36 (s, 2H), 7.04 (m, 2H), 7.32 (dd, J=7.3, 7.6, 1H), 7.41 (d, J=7.9, 1H), 7.50 (m, 5H). Mass spec.: 296.40 (MH)+. After cooling to room temperature the solvents were removed in vacuo the resultant crude dissolved in water (10 mL) followed by addition of ammonium hydroxide until pH 3 The solution was extracted with methylene chloride (3×) The organic layers were pooled together washed with water (2×), brine (2×) dried over sodium sulfate filtered concentrated

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

Procedure: A solution of (2-amino-benzyl)-(1-benzyl-piperidin-4-yl)-amine (1.0 g, 3.39 mmol) and sulfamide (0.64 g, 6.78 mmol) in pyridine was heated at reflux for 14 h. After cooling to room temperature, the solvent was evaporated and the crude product dissolved in water. After being adjusted to pH 9 with 6N sodium hydroxide, the resulting mixture was extracted with methylene chloride (2×). The extracts were washed with water (2×), dried over sodium sulfate, filtered, and concentrated to afford an oily residue which was dissolved in ethyl acetate (4 mL). This solution was mixed with 4N HCl in 1,4-dioxane (2 mL) followed by addition of diethyl ether until precipitation of product occurred. The desired product was obtained by filtration to afford 0.7 g (53%). LC/MS: tR=0.96 min, 358.16 (MH)+. at reflux for 14 h the solvent was evaporated the crude product dissolved in water the resulting mixture was extracted with methylene chloride (2×) The extracts were washed with water (2×) dried over sodium sulfate filtered concentrated to afford an oily residue which

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

Procedure: A solution of (2-amino-benzyl)-(1-benzyl-piperidin-4-yl)-amine (1.0 g, 3.39 mmol) and sulfamide (0.64 g, 6.78 mmol) in pyridine was heated at reflux for 14 h. After cooling to room temperature, the solvent was evaporated and the crude product dissolved in water. After being adjusted to pH 9 with 6N sodium hydroxide, the resulting mixture was extracted with methylene chloride (2×). The extracts were washed with water (2×), dried over sodium sulfate, filtered, and concentrated to afford an oily residue which was dissolved in ethyl acetate (4 mL). This solution was mixed with 4N HCl in 1,4-dioxane (2 mL) followed by addition of diethyl ether until precipitation of product occurred. The desired product was obtained by filtration to afford 0.7 g (53%). LC/MS: tR=0.96 min, 358.16 (MH)+. at reflux for 14 h the solvent was evaporated the crude product dissolved in water the resulting mixture was extracted with methylene chloride (2×) The extracts were washed with water (2×) dried over sodium sulfate filtered concentrated to afford an oily residue which