| Identification | Back Directory | [Name]
1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID | [CAS]
118133-15-6 | [Synonyms]
N-(Ethoxycarbonyl)isonipecoticacid
1-(Ethoxycarbonyl)isonipecotic Acid
1-carbethoxyPiperidine-4-carboxylic acid
1,4-Piperidinedicarboxylic Acid 1-Ethyl Ester
N-(Ethoxycarbonyl)piperidine-4-carboxylicacid
1-(ETHOXYCARBONYL)PIPERIDINE-4-CARBOXYLIC ACID
1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID
4-Carboxy-1-(ethoxycarbonyl)piperidine, Ethyl 4-carboxypiperidine-1-carboxylate | [Molecular Formula]
C9H15NO4 | [MDL Number]
MFCD07339354 | [MOL File]
118133-15-6.mol | [Molecular Weight]
201.22 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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 |
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