69698-56-2

Basic information

• Product Name: Chloroquine diphosphate
• Synonyms: Chloroquine phosphate; 3377 RP; 7-Chlor-4-(4-diaethylamino)-1-methylbutylamino)-chinolindiphosphat; 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2); AI3-14952; Alermine; Aralen diphosphate; Aralen phosphate; Arechin; Avloclor; Chlorochin diphosphate; UNII-6E17K3343P; dl-Chloroquine diphosphate; Chloroquine bis(phosphate); Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-, phosphate (1:2) (8CI); Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-, diphosphate; N~4~-(7-chloroquinolin-4-yl)-N~1~,N~1~-diethylpentane-1,4-diamine phosphate (1:2); chloroquin Phosphate
• CAS NO: 69698-56-2
• Molecular Formula: C18H32ClN3O8P2
• Molecular Weight: 515.862502
• EINECS: 200-055-2
• Mol File: 69698-56-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 200℃
• Boiling Point: 460.6°C at 760 mmHg
• Flash Point: 232.3°C
• Appearance: /
• Vapor Pressure: 1.15E-08mmHg at 25°C
• CAS DataBase Reference: Chloroquine diphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Chloroquine diphosphate(69698-56-2)
• EPA Substance Registry System: Chloroquine diphosphate(69698-56-2)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S22:; S24/25:
• Hazardous Substances Data: 69698-56-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)

Upstream product

• 54-05-7 Chloroquine 
• 50-63-5 chloroquine phosphate 
• 105-14-6 5-diethylamino-2-pentanone 
• 86-98-6 4,7-dichloroquinoline 
• 67459-50-1 (R)-(-)-4-amino-1-(diethylamino)pentane 
• 140-80-7 5-diethylamino-2-pentylamine 
• 54-05-7 (R)-(-)-chloroquine 
• 67459-52-3 (S)-N¹,N¹-diethylpentane-1,4-diamine 

Relevant articles and documents

Preparation method and application of chiral chloroquine and phosphate thereof

The invention discloses a preparation method and application of chiral chloroquine and phosphate thereof. The method comprises the following steps: in a resolving solvent, salifying and crystallizing chloroquine racemate and a resolving agent to separate out crystals; performing primary recrystallizing, dissociating the crystals in an alkaline solution; filtering and separating out the resolving agent; performing extracting with an organic solvent, and drying and concentrating organic phases to respectively obtain corresponding (R)/(S)-chloroquine; and further salifying the (R)/(S)-chloroquine with phosphoric acid in the solvent to respectively obtain corresponding (R)/(S)-chloroquine phosphate. By adopting the method provided by the invention, the optical purity ee value of a finished product can be greater than 80% after primary crystallization, and the product with higher purity can be obtained by primary recrystallization. The crystals are good in crystal form and easy to filter and separate; the method is simple and convenient in resolution operation, free of tedious purification processes such as column separation, high in product optical purity, and relatively high in yield; and the resolving agent is reusable, so that production cost is low, and the method has a good industrial application prospect.

Asymmetric synthesis method of (S)-chloroquine phosphate

The invention provides a novel asymmetric synthesis method of (S) chloroquine. According to the invention, 5-(N-diethylamino)-2-pentanone and (S)-alpha-methyl benzylamine are adopted as raw materials,and in the presence of Lewis acid, an asymmetric reductive amination reaction is carried out to obtain (S,S)-5-(N'-diethylamino)-N-((1-phenyl)ethyl)-2-pentylamine, catalytic hydrogenation is performed to remove benzyl to obtain a side chain (S)-5-(N'-diethylamino)-2-amyl amine for synthesizing chloroquine, the (S)-5-(N'-diethylamino)-2-amyl amine is condensed with 4,7-dichloroquinoline to obtain(S)-chloroquine, salifying is performed with phosphoric acid, and recrystallizing is performed to obtain (S)-chloroquine phosphate with ee value of more than 99%, wherein the the total yield of the four-step reaction exceeds 70%; and the preparation method is stable, reliable, economical, efficient and easy to industrialize.

Preparation method of chloroquine phosphate

The invention discloses a preparation method of chloroquine phosphate, namely 7-chloro-4-(4-diethylamino-1-methylbutylamino)quinoline diphosphate. The preparation method comprises the following steps: (1) carrying out a condensation reaction on 4,7-dichloroquinoline and 2-amino-5-diethylaminopentane, and carrying out alkalization extraction, concentration and crystallization to obtain chloroquine; and (2) salifying the chloroquine obtained in the step (1) and phosphoric acid to obtain chloroquine phosphate. The method avoids the use of phenol, is simple in reaction, and is beneficial to industrial production; and the chloroquine is crystallized to improve the purity and then salified with the phosphoric acid, so product appearance is good, the purity of the produced chloroquine phosphate is greater than or equal to 99.5%, and a single impurity is less than 0.1% (according to an HPLC area normalization method).