|
|
| | 1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID Basic information |
| Product Name: | 1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID | | Synonyms: | 1-carbethoxyPiperidine-4-carboxylic acid;1-(ETHOXYCARBONYL)PIPERIDINE-4-CARBOXYLIC ACID;1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID;4-Carboxy-1-(ethoxycarbonyl)piperidine, Ethyl 4-carboxypiperidine-1-carboxylate;1,4-Piperidinedicarboxylic Acid 1-Ethyl Ester;N-(Ethoxycarbonyl)isonipecoticacid;N-(Ethoxycarbonyl)piperidine-4-carboxylicacid;1-(Ethoxycarbonyl)isonipecotic Acid | | CAS: | 118133-15-6 | | MF: | C9H15NO4 | | MW: | 201.22 | | EINECS: | | | Product Categories: | | | Mol File: | Mol File |  |
| | 1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID Chemical Properties |
| Melting point | 68-70 | | Boiling point | 343.0±35.0 °C(Predicted) | | density | 1.227 | | storage temp. | Sealed in dry,Room Temperature | | form | powder to crystal | | pka | 4.56±0.20(Predicted) | | color | White to Light yellow |
| Hazard Codes | Xi | | HazardClass | IRRITANT | | HS Code | 2933399990 |
| | 1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID Usage And Synthesis |
| Uses | 1,4-Piperidinedicarboxylic Acid 1-Ethyl Ester, is an starting material in the synthesis of Risperidone (R525000), which is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist. | | Synthesis | Example 1- Preparation of 1-(ethoxycarbonyl)piperidine-4-carboxylic acid
Sodium hydroxide (154.8 g) was dissolved in pure water (750 ml) at 0-10°C and isopiperidine carboxylic acid (250 g) was added. Subsequently, ethyl chloroformate (231 ml) was added slowly and dropwise at 5-20°C. The reaction mixture was warmed up to 20-30°C and maintained at this temperature for 3 hours. Upon completion of the reaction, the reaction solution was acidified with hydrochloric acid to pH 1-2. Toluene (750 ml) was added to the reaction solution and stirred at 25-30 °C for 15 min. The organic layer was separated and concentrated under reduced pressure at below 70 °C to give a residue. The residue was mixed with cyclohexane (1250 ml), heated to 60-70 °C then cooled to 25-30 °C and kept for 1 hour. The resulting solid was filtered, washed with cyclohexane (1250 ml) and dried at 50-55 °C. Yield: 92%. | | References | [1] Patent: WO2014/83571, 2014, A1. Location in patent: Page/Page column 17
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4680 - 4692
[3] Patent: US5663200, 1997, A
[4] Archiv der Pharmazie, 2016, p. 614 - 626 |
| | 1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID Preparation Products And Raw materials |
|