ChemicalBook--->CAS DataBase List--->118133-15-6

118133-15-6

118133-15-6 Structure

118133-15-6 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Hazard Codes ]

Xi
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Hazard InformationBack 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]

Isonipecotic acid

498-94-2

Ethyl chloroformate

541-41-3

1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID

118133-15-6

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
Spectrum DetailBack Directory
[Spectrum Detail]

1-(ETHOXYCARBONYL)-4-PIPERIDINECARBOXYLIC ACID(118133-15-6)1HNMR
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