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

Relevant articles and documents

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 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.

Synthesis method of high-purity chloroquine phosphate

The invention relates to the technical field of medicine synthesis, in particular to a synthesis method of chloroquine phosphate, and particularly provides a synthesis method of high-purity chloroquine phosphate. The synthesis method comprises the following steps: (1) condensation: reacting 4, 7-dichloroquinoline with 2-amido-5-diethylamine pentane to obtain a chloroquine crude product; and (2) refining: recrystallizing to obtain chloroquine with higher purity. (3) salifying: stirring and crystallizing the refined chloroquine and phosphoric acid for 2-3 hours, and filtering to obtain a chloroquine phosphate crude product; and (4) purification: recrystallizing the chloroquine phosphate crude product to obtain high-purity chloroquine phosphate. The method is high in atom utilization rate, high in yield, high in product purity, less in solid waste, beneficial to environmental protection and convenient for industrial application, and has a relatively good industrial prospect.