146801-00-5

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester
• Synonyms: 4-chlorocarbonyl-1-ethoxycarbonyl-piperidine;4-chlorocarbonylpiperidine-1-carboxylic acid ethyl ester;N-ethoxycarbonyl isonipecotyl chloride;Ethyl 4-(Chlorocarbonyl)-1-piperidinecarboxylate
• CAS NO: 146801-00-5
• Molecular Formula: C9H14ClNO3
• Molecular Weight: 219.668
• Mol File: 146801-00-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 291.9±33.0 °C(Predicted)
• Density: 1.235±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester(146801-00-5)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester(146801-00-5)

Safety Data

• Hazardous Substances Data: 146801-00-5(Hazardous Substances Data)

Usage

Description

1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester, also known as Ethyl 4-(Chlorocarbonyl)-1-piperidinecarboxylate, is an organic compound that serves as a crucial intermediate in the pharmaceutical industry. It is characterized by its chemical structure, which includes a piperidine ring with a chlorocarbonyl group at the 4-position and an ethyl ester group. 1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester plays a significant role in the synthesis of various pharmaceuticals due to its unique reactivity and functional groups.

Uses

Used in Pharmaceutical Industry:
1-Piperidinecarboxylic acid, 4-(chlorocarbonyl)-, ethyl ester is used as an intermediate in the preparation of Risperidone (R525000), a potent antipsychotic medication. Risperidone is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist, which makes it effective in treating various psychiatric disorders, including schizophrenia and bipolar disorder. The compound's role in the synthesis of Risperidone highlights its importance in the development of novel therapeutic agents for mental health conditions.

Upstream product

• 498-94-2 isonipecotic acid 
• 118133-15-6 1-ethoxycarbonylpiperidine-4-carboxylic acid 

Downstream Products

• 153355-41-0 [(3-bromo-2-[(1-ethoxycarbonylpiperid-4-yl)carbonyloxy]-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride 
• 934694-96-9 2,4,6-trimethyl-N-[8-(5-piperidin-4-ylmethyl-thien-2-yl)octyl]benzenesulfonamide 
• 934694-95-8 4-{5-[8-(2,4,6-trimethylbenzenesulfonylamino)octyl]thieno-2-carbonyl}piperidine-1-carboxylic acid ethyl ester 
• 844488-27-3 ethyl 4-[(1-benzyl-1H-imidazol-2-yl)carbonyl]-1-piperidinecarboxylate 

Relevant articles and documents

Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands

Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D2 receptor (D2DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D2DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of Ki = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D2DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D2DAR is more stable.

Process for the manufacture of brofaromine and analogs thereof

A process for the manufacture of brofaromine and analogues thereof by reaction of a trisubstitued phosphonium methyl dihydroquinone compound with a 1-(substituted carbonyl)-4-(substituted carbonyl)-piperidine with subsequent cyclization and hydrolysis of the remaining carbonyl substituent. The resulting prmary compound can be further interconverted between free and salt forms or between different salt forms as desired.