ChemicalBook CAS DataBase List 1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID

1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID synthesis

5synthesis methods

Product Name:1-BENZYLPIPERIDINE-3-CARBOXYLIC ACID
CAS Number:141943-04-6
Molecular formula:C13H17NO2
Molecular Weight:219.28

72551-53-2

141943-04-6

The general procedure for the synthesis of 1-benzylpiperidine-3-carboxylic acid from ethyl 1-benzylpiperidine-3-carboxylate was as follows: a 4N aqueous sodium hydroxide solution (15 ml) was slowly added to a mixture of tetrahydrofuran (30 ml) and 1,4-dioxane (30 ml) containing ethyl 1-benzyl-3-piperidinecarboxylate (7.00 g, 28.3 mmol). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, 4N aqueous sodium hydroxide solution (15 ml) was added again and stirring was continued at room temperature overnight. After completion of the reaction, 2N hydrochloric acid (15 ml) was slowly added to neutralize the reaction solution under ice bath cooling conditions. The neutralized mixture was azeotropically dehydrated using toluene. The obtained residue was suspended in ethanol and after filtration, the filtrate was concentrated to finally obtain 1-benzyl-3-piperidine carboxylic acid (6.3 g, 100% yield).

72551-53-2 Synthesis

72551-53-2
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141943-04-6
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Yield:141943-04-6 100%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;1,4-dioxane;water at 20;

Steps:

138.b Example 138; Synthesis of N-(1-benzylpiperidin-3-yl)-1H-indazole-5-carboxamide; (b) Synthesis of 1-benzyl-3-piperidinecarboxylic 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, 100%).

References:

EP1403255,2004,A1 Location in patent:Page 66