Check patentability & draft patents in minutes with Patsnap Eureka AI!

Process for preparing 4-phenyl cycloheptylamine

A preparation process, phenyl technology, is applied in the field of preparation of pharmaceutical and chemical intermediate 4-phenylcycloheptylamine, which can solve the problems of expensive quotation and no literature report on the preparation method of the intermediate, and achieve low preparation cost and simple operation , the effect of high reaction yield

Inactive Publication Date: 2018-11-20
AFFILIATED HOSPITAL OF ZUNYI MEDICAL COLLEGE
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The price of 4-phenylcycloheptylamine, a pharmaceutical intermediate, is relatively expensive in several chemical reagent companies such as Acros. After searching the literature, it is found that no literature has reported the preparation method of this intermediate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for preparing 4-phenyl cycloheptylamine
  • Process for preparing 4-phenyl cycloheptylamine
  • Process for preparing 4-phenyl cycloheptylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0017] The preparation of embodiment 1.4-phenylcyclohexanone oxime 1

[0018] 4-Phenylcyclohexanone (100g, 0.57mol), hydroxylamine hydrochloride (100g, 1.44mol) and 50% aqueous potassium hydroxide solution (150mL) were added to ethanol (50mL), and the resulting mixture was heated to reflux for 2 hours , concentrated in vacuo, added water, and stirred to obtain a white precipitate. The crude product of the target product was obtained after collecting the filter cake by filtration, and the crude product was recrystallized from ethanol to obtain 4-phenylcyclohexanone oxime 1 (106 g, 0.56 mol) as a white solid. 1H NMR (400MHz, CDCl3) δ=1.62-1.72(m,2H),1.86-1.91(m,1H),1.89-1.91(m,2H),2.27-2.31(m,1H),2.53-2.57(m ,1H),2.75-2.82(m,1H),3.46-3.51(m,1H),7.20-7.33(m,5H).

Embodiment 2

[0019] The preparation of embodiment 2.4-phenylcaprolactam 2

[0020] 4-Phenylcyclohexanone oxime 1 (50 g, 0.26 mol) and polyphosphoric acid (500 g) were put into a 1L round bottom flask, and the mixture was heated to 120° C. and stirred for 30 min. The reaction solution was slowly poured into ice water, stirred until the polyphosphoric acid was completely dissolved in the water, and the target product was recovered by CH2Cl2 extraction (200mL×3). The combined CH2Cl2 extracts were dried with anhydrous Na2SO4, and 4-phenylcaprolactam 2 (48 g, 0.25 mol) was obtained as a white solid after rotary evaporation under reduced pressure. 1H NMR (400MHz, CDCl3) δ=1.71-1.78(m,2H),2.00-2.03(m,2H),2.58-2.63(m,2H),2.74-2.78(m,1H),3.30-3.40(m ,2H),6.41(br,1H),7.16-7.33(m,5H).

Embodiment 3

[0021] The preparation of embodiment 3.4-phenyl cycloheptylamine 3

[0022] 4-Phenylcaprolactam 2 (48g, 0.25mol) was dissolved in 150mL of tetrahydrofuran, and LiAlH4 (35g.0.92mol) was added in batches under stirring; the resulting mixture was heated to reflux and stirred for 4h. After the reaction solution was cooled to room temperature, 15 mL of water was slowly added to quench the reaction, and the mixture was stirred at room temperature for 30 min, forming a large amount of white precipitate; filtered, and the filter cake was fully washed with THF. The organic layer was dried with anhydrous Na2SO4, and 4-phenylcycloheptylamine 3 (42 g, 0.24 mol) was obtained as a light yellow liquid after rotary evaporation under reduced pressure. 1H NMR (400MHz, CDCl3) δ=1.71-1.99 (m, 7H), 2.87-2.91 (m, 3H), 3.04-3.09 (m, 2H), 7.14-7.30 (m, 5H); ESI-MS 176 ( MH)+; HPLC-Purity>97%.

[0023] HPLC determination conditions:

[0024] Chromatographic column: Agela Venusil MP C-18 (5μm, 4.6×1...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention discloses a process for preparing 4-phenyl cycloheptylamine. The process comprises the following steps: 1) in the presence of a strong base, condensing 4-phenyl cyclohexanone and hydroxylammonium chloride in an appropriate solvent at an appropriate temperature so as to obtain 4-phenyl cyclohexanone-oxime 1; 2) carrying out a rearrangement reaction on the compound 1 in polyphosphoricacid at an appropriate temperature so as to obtain 4-phenyl caprolactam 2; and 3) carrying out a reduction reaction on the compound 2 and lithium aluminum hydride in an appropriate solvent at an appropriate temperature, thereby obtaining a compound 3. The preparation process disclosed by the invention has the advantages that initial raw materials and reaction agents used in the preparation processare all common reagents which are low in price and easy to obtain, yields of different steps of reactions are high, aftertreatment is simple to operate, the overall yield of a target product is high,the preparation cost is low, and industrial production requirements can be met.

Description

technical field [0001] The invention belongs to the field of organic chemical industry, and in particular relates to a preparation process of medicine and chemical intermediate 4-phenylcycloheptylamine. Background technique [0002] Cycloheptylamine and its substituted derivatives are important pharmaceutical and chemical intermediates with various biological activities or chemical functions. Incadronate disodium, which was launched in 1997, is a bisphosphonate drug derived from cycloheptylamine. It is used for malignant tumors complicated with hypercalcemia, and the therapeutic effect is remarkable. Such biogenic amines are also widely found in fermented foods, fermented beverages and wine. [0003] In recent years, multiple molecular structures containing 4-phenylcycloheptylamine fragments have been studied, showing diverse biological activities such as anti-tumor, HIV virus and bacterial infection. Shen H-C reported a benzimidazole pyrrolidone amide synthesized from 4-p...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D223/04
CPCC07D223/04
Inventor 王玉和夏同霞赵长阔徐浪
Owner AFFILIATED HOSPITAL OF ZUNYI MEDICAL COLLEGE
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com