858676-60-5

Basic information

• Product Name: 1-(4-IODOBENZYL)PYRROLIDINE
• Synonyms: 1-(4-IODOBENZYL)PYRROLIDINE;1-(4-Iodobenzyl)pyrrolidine 97%;1-(4-Iodobenzyl)pyrrolidine97%
• CAS NO: 858676-60-5
• Molecular Formula: C₁₁H₁₄IN
• Molecular Weight: 287.14
• Mol File: 858676-60-5.mol

Chemical Properties

• Boiling Point: 288.2 °C at 760 mmHg
• Flash Point: 128.1 °C
• Appearance: /
• Density: 1.593g/cm³
• Vapor Pressure: 0.00237mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 1-(4-IODOBENZYL)PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-IODOBENZYL)PYRROLIDINE(858676-60-5)
• EPA Substance Registry System: 1-(4-IODOBENZYL)PYRROLIDINE(858676-60-5)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 858676-60-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(4-IODOBENZYL)PYRROLIDINE is used as a building block in organic synthesis for the preparation of various biologically active molecules. Its unique structure allows for the creation of a wide range of compounds with potential applications in different fields.
Used in Pharmaceutical Research:
In pharmaceutical research, 1-(4-IODOBENZYL)PYRROLIDINE is employed as a key component in the development of new drugs. Its versatility and reactivity make it an essential tool for medicinal chemists working on the design and synthesis of novel therapeutic agents.
Used as an Intermediate in Pharmaceutical Production:
1-(4-IODOBENZYL)PYRROLIDINE is utilized as an intermediate in the production of pharmaceuticals. Its presence in the synthesis process contributes to the formation of the final drug product, highlighting its importance in the pharmaceutical industry.
Used as an Intermediate in Agrochemical Production:
Similarly, 1-(4-IODOBENZYL)PYRROLIDINE is used as an intermediate in the production of agrochemicals. Its role in the synthesis of these chemicals is vital for the development of effective products for agricultural applications.

InChI:InChI=1/C11H14IN/c12-11-5-3-10(4-6-11)9-13-7-1-2-8-13/h3-6H,1-2,7-9H2

Upstream product

• 123-75-1 pyrrolidine 
• 619-58-9 4-iodobenzoic acid 
• 168317-99-5 (4-iodophenyl)(pyrrolidin-1-yl)methanone 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 16004-15-2 1-bromomethyl-4-iodobenzene 

Downstream Products

• 630385-38-5 1-[1-(4-iodophenyl)-1-(methyl)ethyl]pyrrolidine 
• 1394862-48-6 1,3-bis(2-(4-(pyrrolidin-1-ylmethyl)phenyl)oxazol-5-yl)benzene 
• 858677-31-3 1-{4-[(trimethylsilyl)ethynyl]benzyl}pyrrolidine 

Relevant articles and documents

A practical catalytic reductive amination of carboxylic acids

We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.

Direct Catalytic Reductive N-Alkylation of Amines with Carboxylic Acids: Chemoselective Enamine Formation and further Functionalizations

Direct reductive N-alkylation of secondary amines with carboxylic acids using molybdenum hexacarbonyl (5 mol %) as catalyst and diethoxymethylsilane as reducing agent generate enamines in a straightforward fashion in high yields. The formed enamines are without the need for isolation or purification further reacted with trimethylsilyl cyanide in the same reaction flask to yield α-amino nitriles in good yields. In the optimized reaction conditions equimolar amounts of carboxylic acid and amine are reacted under neat conditions, and a catalytic amount of trifluoroethanol (0.1 mol %) is added along with TMSCN for the cyanation step. The reductive N-alkylation reaction is demonstrated to be highly chemoselective, tolerating a multitude of different functional groups present in the starting carboxylic acids and amines. The reaction is scalable and the generated α-amino nitriles are converted to other useful compounds, e.g., α-amino acids or amino-tetrazoles. In addition, the intermediate enamines are further transformed into triazolines, sulfonylformamidines, pyrimidinediones, and TMS-propargylamines, respectively, in high yields under mild reaction conditions. Benzoic acids react with secondary amines under similar conditions to give tertiary amines in high yields, and using this methodology, the biologically active compound Piribedil was isolated in 80% yield in a direct one-pot reaction setup.

Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines

A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.

Orally bioavailable factor Xa inhibitors containing alpha-substituted gem-dimethyl P4 moieties

In an effort to identify a potential back-up to apixaban (Eliquis), we explored a series of diversified P4 moieties. Several analogs with substituted gem-dimethyl moieties replacing the terminal lactam of apixaban were identified which demonstrated potent

3-(4-PIPERIDINE-1YLMETHYL-PHENYL)-PROPION ACID-PHENYLAMIDE-DERIVATIVES AND RELATED COMPOUNDS USED IN THE FORM OF MCH ANTAGONISTS (MELANINE CONCENTRATING HORMONE) FOR TREATING EATING DISORDERS

The invention relates to amid compounds of general formula (I), wherein groups and residuals A, B, b, W, X, Y, Z, R1, R2 and R3 have significances given in a claim 1. In addition, said invention relates to drugs containing at least one type of inventive amid. Because of the antagonist activity of an MCH-receptor, the inventive drugs are suitable for treating metabolic disturbances and/or eating disorders, in particular adiposity, bulimia, anorexia, hyperphagia and diabetes.