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

• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 1284448-67-4 isopropyl 4-(4-bromophenyl)-4-oxobutanoate 
• 1476776-39-2 isopropyl 3-(2-(4-bromophenyl)oxiran-2-yl)-propanoate 
• 1476776-40-5 isopropyl 4-(4-bromophenyl)-5-oxopentanoate 
• 1476776-44-9 (S)-5-(4-bromophenyl)piperidin-2-one 
• 108-86-1 bromobenzene 
• 1008-88-4 3-phenylpyridine 
• 129013-83-8 3-(4-bromophenyl)pyridine 
• 769944-72-1 3-(4-bromo-phenyl)-piperidine 
• 160678-57-9 (R)-3-(4-bromophenyl)cyclopentan-1-one 
• 930-30-3 cyclopent-2-enone 
• 1196713-21-9 (3S)-3-(4-aminophenyl)piperidine 
• 3973-62-4 3-phenylpiperidine 
• 3979-67-7 N-benzyl-3-phenylpiperidine 

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.

Niraparib intermediate, preparation method and application thereof, and synthesis method of niraparib

The invention relates to a compound alpha-(3-aminopropyl)-p-bromophenylacetic acid, a preparation method and application thereof, (S)-3-(4-bromophenyl)-piperidine-2-one, a preparation method and application thereof, and synthesis methods of (S)-3-(4-bromophenyl)-piperidine) p-toluenesulfonate, N-Boc-(3S)-(4-bromophenyl)piperidine and niraparib. 4-bromophenylacetate 5 is used as a raw material, a nucleophilic reaction is carried out on the raw material and a nitrogen source reagent 4 under the action of an alkali to generate a compound 6; the compound 6 is subjected to deprotection and hydrolysis to obtain an amino acid compound 7; and the amino acid compound 7 is subjected to chiral column separation or chemical resolution to obtain compounds 8 and 9; and the separated enantiomer 8 can besubjected to racemization and resolution conversion (or chiral column separation) to obtain a compound 9, and the process material cost is greatly reduced. After the compound 9 is obtained, a compound1 can be obtained through conventional condensation reaction ring closing, reduction and BOC loading. Splitting operation is advanced, and the enantiomer 8 is subjected to racemization recovery treatment and is repeatedly applied to different splitting batches to continuously obtain the product 9, so the process material cost is lower.

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