56824-22-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(2-Chloroethyl)-N-methyl-pyrrolidine hydrochloride is used as an intermediate for the synthesis of reversed lactam analogues of ARC-111, which possess potent topoisomerase I-targeting activity and cytotoxicity. These analogues are valuable in the development of anticancer drugs due to their ability to inhibit cancer cell growth by targeting the topoisomerase I enzyme.
Used in Organic Chemistry:
In the field of organic chemistry, 2-(2-Chloroethyl)-1-methylpyrrolidine hydrochloride is utilized as a reagent in the synthesis of N-[2-(1-methylpyrrolidin-2-yl)ethyl]-N-(2-iodo-4,5-dimethoxyphenyl) amide. 2-(2-Chloroethyl)-N-methyl-pyrrolidine hydrochloride is an important building block for the creation of more complex molecular structures with potential applications in various industries, including pharmaceuticals and materials science.
Used in the Synthesis of 1-Methyl-2-[2-[2-(2-Phenylethyl)Phenoxy]Ethyl]Pyrrolidine Hydrochloride:
2-(2-Chloroethyl)-N-methyl-pyrrolidine hydrochloride is also employed in the synthesis of 1-methyl-2-[2-[2-(2-phenylethyl)phenoxy]ethyl]pyrrolidine hydrochloride, a compound with potential applications in the pharmaceutical industry. The chloroethyl group in the intermediate allows for further functionalization and the creation of diverse molecular structures with specific biological activities.

InChI:InChI=1/C7H14ClN.ClH/c1-9-6-2-3-7(9)4-5-8;/h7H,2-6H2,1H3;1H

Upstream product

• 61810-78-4 (-)-2-((S)-1-methylpyrrolidin-2-yl)ethanol 
• 56502-01-3 (2S)-1-tert-butoxycarbonyl-2-carboxymethylpyrrolidine 
• 67004-64-2 2-(1-methyl-2-pyrrolidine)ethanol 
• 1352748-96-9 (S)-ethyl 2-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 60307-26-8 R(+)-1-methyl-2-(2-hydroxyethyl)pyrrolidine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of 3,4-dihydroquinolin-2(1 H)-one and 1,2,3,4-tetrahydroquinoline-based selective human neuronal nitric oxide synthase (nNOS) inhibitors

Neuronal nitric oxide synthase (nNOS) inhibitors are effective in preclinical models of many neurological disorders. In this study, two related series of compounds, 3,4-dihydroquinolin-2(1H)-one and 1,2,3,4- tetrahydroquinoline, containing a 6-substituted thiophene amidine group were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). A structure-activity relationship (SAR) study led to the identification of a number of potent and selective nNOS inhibitors. Furthermore, a few representative compounds were shown to possess druglike properties, features that are often difficult to achieve when designing nNOS inhibitors. Compound (S)-35, with excellent potency and selectivity for nNOS, was shown to fully reverse thermal hyperalgesia when given to rats at a dose of 30 mg/kg intraperitonieally (ip) in the L5/L6 spinal nerve ligation model of neuropathic pain (Chung model). In addition, this compound reduced tactile hyperesthesia (allodynia) after oral administration (30 mg/kg) in a rat model of dural inflammation relevant to migraine pain.

Preparation method of clomastine fumarate with high chiral purity

The invention discloses a preparation method of chlormastine fumarate with high chiral purity. The preparation method comprises the following five steps: step 1, taking D-arginine as a resolving agentto resolve a compound N-methyl-2-(2-hydroxyethyl) pyrrolidine shown in a formula 2 to obtain a compound shown in a formula 3; step 2, reacting the compound shown in the formula 3 with thionyl chloride for chlorination to obtain a compound shown in a formula 4; step 3, reacting the compound shown in the formula 4 with a compound 1-((4-chlorphenyl)-1-phenyl) ethanol shown in a formula 5 under the condition that sodium amide is strong base to obtain a compound shown in a formula 6; step 4, resolving the compound shown in the formula 6 by adopting tartaric acid to remove chiral isomer impurities,and obtaining a compound shown in a formula 7 at the same time; and step 5, salifying the compound shown in the formula 7 and fumaric acid to obtain a compound chlormastine fumarate shown in a formula 1. The prepared clomastine fumarate bulk drug has high chiral purity, the product quality meets the injection drug requirements specified in pharmacopeia, the technological process is simple and easy to control, the operability is high, and industrial production can be achieved.

Asymmetric synthesis of H1 receptor antagonist (R,R)-clemastine

The first asymmetric synthesis of (R,R)-clemastine (1) has been accomplished by the coupling of (R)-tertiary alcohol 2 and (R)-chloroethylpyrrolidine 3 via O-alkylation. (R)-Tertiary alcohol 2 was synthesized by stereoselective alkylation of chiral α-benz

Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate

The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement.

SUBSTITUTED BENZHYDRYLETHERS

Disclosed herein are substituted benzhydrylethers of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of their use thereof.