1335523-82-4

Basic information

• Product Name: (S)-3-(4-Bromophenyl)piperidine
• Synonyms: (S)-3-(4-Bromophenyl)piperidine;(3S)-3-(4-Bromophenyl)piperidine
• CAS NO: 1335523-82-4
• Molecular Formula: C₁₁H₁₄BrN
• Molecular Weight: 240.13956
• EINECS: -0
• Mol File: 1335523-82-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 310.9±35.0 °C(Predicted)
• Appearance: /
• Density: 1.313±0.06 g/cm3(Predicted)
• PKA: 9.90±0.10(Predicted)
• CAS DataBase Reference: (S)-3-(4-Bromophenyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-Bromophenyl)piperidine(1335523-82-4)
• EPA Substance Registry System: (S)-3-(4-Bromophenyl)piperidine(1335523-82-4)

Safety Data

• Hazardous Substances Data: 1335523-82-4(Hazardous Substances Data)

Usage

Description

(S)-3-(4-Bromophenyl)piperidine is an organic compound that serves as a crucial intermediate in the synthesis of pharmaceuticals, particularly in the development of targeted cancer therapies. It is characterized by its unique molecular structure, which includes a piperidine ring and a bromophenyl group, contributing to its specific chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(S)-3-(4-Bromophenyl)piperidine is used as a key intermediate in the synthesis of Niraparib (N481400), a novel oral poly(ADP-ribose) polymerase (PARP) inhibitor. (S)-3-(4-Bromophenyl)piperidine is specifically designed to target and inhibit PARP enzymes, which play a significant role in the repair of DNA damage in cancer cells. By inhibiting PARP, Niraparib enhances the DNA repair deficiency in BRCA-1 and -2 mutant tumors, leading to increased cell death and improved treatment outcomes for patients with these specific genetic mutations.

Upstream product

• 108-86-1 bromobenzene 
• 160678-57-9 (R)-3-(4-bromophenyl)cyclopentan-1-one 
• 930-30-3 cyclopent-2-enone 
• 1196713-21-9 (3S)-3-(4-aminophenyl)piperidine 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 204851-47-8 (4S)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 1598387-46-2 C₁₇H₁₄BrNO₃ 
• 232953-62-7 3-[2-(4-bromophenyl)acetyl]-4-isopropyloxazolidin-2-one 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 1476776-55-2 (S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 1038916-08-3 2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid 
• 1476776-88-1 C₂₄H₂₇N₃O₄ 
• 1196713-67-3 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester 
• 1476776-89-2 C₂₅H₂₉N₃O₄ 
• 1038915-73-9 2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt 
• 1038915-60-4 (3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine 

Relevant articles and documents

Niraparib preparation method

The invention provides a niraparib preparation method, which comprises: carrying out photocatalysis on a compound 1 and bromobenzene under a Pd catalyst to obtain a niraparib key intermediate; carrying out chiral resolution on the niraparib key intermediate, and coupling the niraparib key intermediate with NBoc-1H-indazole-7-carboxamide under the catalysis of copper bromide to obtain protected niraparib; and removing the protective color of the protected niraparib under the action of methanesulfonic acid, and obtaining the target product niraparib under tetrahydrofuran pulping. The preparation method of niraparib is simple in synthesis process route, high in preparation efficiency, small in damage to human bodies and the environment and low in synthesis cost.

Preparation method of niraparib intermediate (S)-3-(4-bromophenyl) piperidine

The invention discloses a preparation method of a niraparib intermediate that is (S)-3-(4-bromophenyl) piperidine, which comprises the following steps: by using chiral 1-phenylethylamine as a raw material, carrying out alkylation, condensation, cyclization and reduction, and finally removing an amino protection group to obtain the (S)-3-(4-bromophenyl) piperidine. The preparation method of the (S)-3-(4-bromophenyl) piperidine has the advantages of short route, few steps, simple and convenient process operation, avoidance of use of dangerous reagents, highly toxic reagents and irritant malodorous reagents, reduction of potential safety hazards to operators, reduction of the operation safety level of production, environmental protection, and facilitation of industrialization.

Preparation method of niraparib intermediate

The invention discloses a preparation method of a niraparib intermediate. The preparation method of the compound represented by formula III is characterized in that a compound represented by formula IV and a compound represented by formula V undergo a sub