1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID

A 4N-aqueous sodium hydroxide solution (15 ml) was added to a solution of ethyl 1-benzyl-3-piperidinecarboxylate (7.00 g, 28.3 mmol) in a mixture of tetrahydrofuran (30 ml) and 1, 4-dioxane (30 ml), and the resulting mixture was stirred at room temperature for 4 hours. After a 4N-aqueous sodium hydroxide solution (15 ml) was added again, the resulting mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was neutralized by the addition of 2N-hydrochloric acid (15 ml) under ice-cooling and the resulting mixture was subjected to azeotropic concentration with toluene. The residue was suspended in ethanol, followed by filtration, and the filtrate was concentrated to obtain 1-benzyl-3-piperidinecarboxylic acid (6.3 g, 100percent).A 4N-aqueous sodium hydroxide solution (15 ml) was added to a solution of ethyl 1-benzyl-3-piperidinecarboxylate (7.00 g, 28.3 mmol) in a mixture of tetrahydrofuran (30 ml) and 1, 4-dioxane (30 ml), and the resulting mixture was stirred at room temperature for 4 hours. After a 4N-aqueous sodium hydroxide solution (15 ml) was added again, the resulting mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was neutralized by the addition of 2N-hydrochloric acid (15 ml) under ice-cooling and the resulting mixture was subjected to azeotropic concentration with toluene. The residue was suspended in ethanol, followed by filtration, and the filtrate was concentrated to obtain 1-benzyl-3-piperidinecarboxylic acid (6.3 g, 100%).Step 1: l-Benzylpiperidine-3-carbonyl chloride hydrochloride; [00273] Hydrochloric acid (20 % aq, 100 mL) was added to ethyl l-benzylpiperidine-3- carboxylate (14.2 g, 57.4 mmol) and the mixture heated at reflux for 4 h. The reaction was cooled and concentrated in vacuo to give l-benzylpiperidine-3-carboxylic acid as a pale yellow solid. This solid was dissolved in thionyl chloride and the resulting solution stirred at room temperature for 1 h. Thionyl chloride was removed in vacuo and the resulting solid was slurried in THF and azeotroped to afford the title compound as a pale yellow solid which was used without further purification (17.0 g, quant.).Triethylamine (0.38 ml, 2.73 mmol) and diphenylphosphoryl azide (0.692 g, 2.52 mmol) were added to a solution of

Molecular Weight:219.28
XLogP3:-0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:219.125928785
Monoisotopic Mass:219.125928785
Topological Polar Surface Area:40.5
Heavy Atom Count:16
Complexity:236
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes