53324-72-4

Basic information

• Product Name: 1-(2-chloroethyl)-2-methylpiperidine
• Synonyms: 1-(2-chloroethyl)-2-methylpiperidine;Einecs 258-477-8
• CAS NO: 53324-72-4
• Molecular Formula: C₈H₁₆ClN
• Molecular Weight: 161.67234
• EINECS: 258-477-8
• Mol File: 53324-72-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 203.3°Cat760mmHg
• Flash Point: 76.8°C
• Appearance: /
• Density: 0.971g/cm³
• Vapor Pressure: 0.279mmHg at 25°C
• Refractive Index: 1.459
• PKA: 8.63±0.10(Predicted)
• CAS DataBase Reference: 1-(2-chloroethyl)-2-methylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroethyl)-2-methylpiperidine(53324-72-4)
• EPA Substance Registry System: 1-(2-chloroethyl)-2-methylpiperidine(53324-72-4)

Safety Data

• Hazardous Substances Data: 53324-72-4(Hazardous Substances Data)

Usage

Description

1-(2-chloroethyl)-2-methylpiperidine, with the chemical formula C8H16ClN, is a colorless liquid chemical compound. It features a piperidine ring with a 2-chloroethyl substituent and a methyl group, which contributes to its versatile applications in various industries.

Uses

Used in Pharmaceutical Industry:
1-(2-chloroethyl)-2-methylpiperidine is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-chloroethyl)-2-methylpiperidine serves as a chemical intermediate, playing a crucial role in the production of pesticides and other agrochemical products that help protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
1-(2-chloroethyl)-2-methylpiperidine is utilized as a reagent in organic synthesis, enabling the preparation of a wide range of compounds with diverse applications.
Used in the Preparation of Functionalized Piperidine Derivatives:
1-(2-chloroethyl)-2-methylpiperidine has been studied for its potential use as a precursor in the synthesis of other functionalized piperidine derivatives. These derivatives may exhibit various biological activities, making them valuable for further research and development in the pharmaceutical and chemical industries.

InChI:InChI=1/C8H16ClN/c1-8-4-2-3-6-10(8)7-5-9/h8H,2-7H2,1H3

Upstream product

• 17719-74-3 1-(2-hydroxyethyl)-2-methylpiperidine 
• 67-66-3 chloroform 
• 109-05-7 2-Methylpiperidin 

Downstream Products

• 74379-67-2 α-(o-fluorophenyl)-α-[2-(diisopropylamino)ethyl]-α-[2-(2-methyl-1-piperidinyl)ethyl]acetamide 

Relevant articles and documents

Preparation and in vitro pharmacology of 5-HT4 receptor ligands. Partial agonism and antagonism of metoclopramide analogous benzoic esters

Alicyclic ester analogues of the gastroprokinetic benzamide metoclopramide (1) and its ester congener SDZ 205557 (2), a 5-HT4 receptor antagonist, were prepared by O-alkylation of 4-amino-5-chloro-2-methoxybenzoate with N-(2-chloroethyl) substituted alicyclic amines. The bromo and iodo analogue of compound 13b (2-(1-piperidinyl)ethyl 4-amino-5-chloro-2-methoxybenzoate) were obtained by halogenation of dechloro-13b with N-halogenated succinimides. The series was evaluated in functional in vitro assays with regard to affinity for serotoninergic 5-HT4, 5-HT3 and muscarinic M3 receptors. The affinities for 5-HT3 and M3 receptors were below 6.0 (pK(B) or pA2). On 5-HT4 receptors in guinea-pig ileal longitudinal muscle and rat oesophagus, the majority of compounds revealed partial 5-HT4 receptor agonism susceptible to blockade by SDZ 205557, a reference 5-HT4 receptor antagonist (pK(B) = 7.25-7.73 (guinea-pig ileum) and 7.09-7.43 (rat oesophagus)). The relative agonist potency was in the range of 5-303% (5-HT: 100%). Compound 13b and its bromo analogue 17 were the most potent esters of the series. The enantiomers of 13g ((R)- and (S)-2-(2-methyl-1-piperidinyl)ethyl 4-amino-5-chloro-2-methoxybenzoate) interacted stereoselectively with 5-HT4 receptors and displayed enantiomeric potency ratios (R)/(S) of 4.3-8.7. There was an excellent correlation between (a) antagonist affinity on guinea-pig ileum and rat oesophagus, (b) relative agonist potency on guinea-pig ileum and rat oesophagus, and (c) between antagonist affinity and relative agonist potency within each assay (r2 > 0.91). The new compounds may serve as academic tools in evaluating the functional role of 5-HT4 receptors. The selective partial 5-HT4 receptor agonists presented in this paper may be useful to restore physiological motility and secretion in the gut with reduced or absent propensity to elicit tachycardia and desensitization of the intestinal target receptor.