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Quetiapine

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Name

Quetiapine

EINECS N/A
CAS No. 111974-69-7 Density 1.27 g/cm3
PSA 73.60000 LogP 2.16740
Solubility N/A Melting Point 172 - 174oC
Formula C21H25N3O2S Boiling Point 556.5 °C at 760 mmHg
Molecular Weight 383.514 Flash Point 290.4 °C
Transport Information N/A Appearance white crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 111974-69-7 (2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol) Hazard Symbols N/A
Synonyms

2-(2-(4-Dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol;Co-Quetiapine;Seroquel;Ethanol,2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-;

Article Data 43

Quetiapine Synthetic route

13349-82-1

1-[2-(2-hydroxyethoxy)ethyl]piperazine

13745-86-3

11-chloro-dibenzo[b,f][1,4]thiazepine

111974-69-7

Quetiapine

Conditions
ConditionsYield
In toluene at 105 - 107℃;99%
In toluene at 110 - 120℃; for 8h; Product distribution / selectivity;98%
In toluene Reflux;92%
13745-86-3

11-chloro-dibenzo[b,f][1,4]thiazepine

(2-(piperazin-1-yl)ethoxy)methanol

111974-69-7

Quetiapine

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;99%
753475-15-9

11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride

628-89-7

2-(2-Chloroethoxy)ethanol

111974-69-7

Quetiapine

Conditions
ConditionsYield
With sodium carbonate; sodium iodide; tetrabutylammomium bromide In toluene at 115 - 120℃; for 17h; Heating / reflux;98.2%
With sodium carbonate; sodium iodide; tetrabutylammomium bromide In butan-1-ol at 115 - 120℃; for 17h; Heating / reflux;96.9%
With sodium carbonate; sodium iodide In butan-1-ol at 115 - 120℃; for 17h; Heating / reflux;94.1%

11-{4-[2-(2-tritiloxiethoxy)ethyl]piperazine-1-yl}dibenzo[b,f][1,4]thiazepine

111974-69-7

Quetiapine

Conditions
ConditionsYield
Stage #1: 11-{4-[2-(2-tritiloxiethoxy)ethyl]piperazine-1-yl}dibenzo[b,f][1,4]thiazepine With toluene-4-sulfonic acid In methanol; toluene for 4h; Heating / reflux;
Stage #2: With hydrogenchloride In water; toluene
Stage #3: With sodium hydroxide In water; toluene pH=9.5; Product distribution / selectivity;
95%
849790-30-3

2-nitro-2'-[4-[2-(2-hydroxyethoxy)ethyl]-piperazinylcarbonyl]diphenylsulfide

111974-69-7

Quetiapine

Conditions
ConditionsYield
With formic acid; iron at 85 - 90℃;94.5%
844639-07-2

11-[4-[2-(2-(2-acetyloxy)ethoxy)ethyl]-1-piperazinyl]dibenzo [b,f][1,4]thiazepine

111974-69-7

Quetiapine

Conditions
ConditionsYield
Stage #1: 11-[4-[2-(2-(2-acetyloxy)ethoxy)ethyl]-1-piperazinyl]dibenzo [b,f][1,4]thiazepine With potassium hydroxide In methanol at 20 - 25℃; for 3h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water pH=10; Product distribution / selectivity;
94%
With sodium hydroxide In ethanol; water at 20℃; for 0.5h;
With sodium hydroxide; water In methanol at 160℃;
3159-07-7

dibenzo[b,f][1,4]thiazepin-11-one

111974-69-7

Quetiapine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3; N,N-dimethylaniline / 4 h / Heating
2: xylene / Heating
View Scheme
Multi-step reaction with 2 steps
1: pyrophosphoryl chloride; N,N-dimethyl-aniline / toluene / 4.5 h / 110 - 112 °C / Green chemistry
2: toluene / 105 - 107 °C
View Scheme
844639-08-3

11-{4-[2-(2-benzyloxy-ethoxy)ethyl]-piperazin-1-yl}-dibenzo[b,f][1,4]thiazepine

111974-69-7

Quetiapine

Conditions
ConditionsYield
Stage #1: 11-{4-[2-(2-benzyloxy-ethoxy)ethyl]-piperazin-1-yl}-dibenzo[b,f][1,4]thiazepine With boron trichloride In toluene; xylene at -5 - 20℃; for 2h;
Stage #2: With triethylamine In methanol; toluene; xylene for 0.166667h;
Stage #3: With sodium hydroxide In methanol; water; toluene; xylene Product distribution / selectivity;

benzoic acid 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-piperazin-1-yl)-ethoxy]-ethyl ester

111974-69-7

Quetiapine

Conditions
ConditionsYield
Stage #1: benzoic acid 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-piperazin-1-yl)-ethoxy]-ethyl ester With sodium hydroxide In ethanol; water at 80℃; for 2h;
Stage #2: With hydrogenchloride In water; ethyl acetate
Stage #3: With sodium hydroxide In water pH=12;
5747-48-8

11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine

17976-70-4

2-(2-hydroxyethoxy)acetaldehyde

111974-69-7

Quetiapine

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium acetate In water; acetic acid at 0 - 10℃; for 1.66667h;
With magnesium borohydride; sodium acetate In water; acetic acid at 0 - 10℃; for 1.66667h;

Quetiapine History

In 1997,Quetiapine was  indicated  to treat  schizophrenia by the U.S. Food and Drug Administration.
In 2004,Quetiapine received  indication for the treatment of mania-associated bipolar disorder.
In 2005, for the treatment of schizophrenia,the New England Journal of Medicine  showed that Quetiapine and other antipsychotics were no more effective than perphenazine (Trilafon), However, the subsequent CATIE trial, funded by AstraZeneca and other major pharmaceutical manufacturers, contradicted the 2005 study in certain instances.
On January 2007,Quetiapine's efficacy has been proved in treating generalized anxiety disorder and major depressive disorder.
 September 2011,it will allow other companies to manufacture and market quetiapine,because the AstraZeneca's patent for Seroquel  will be expire in the United States.

Quetiapine Specification

The Quetiapine, with the CAS registry number 111974-69-7, is also known as Ethanol,2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-. It belongs to the product category of Quetiapine. This chemical's molecular formula is C21H25N3O2S and molecular weight is 383.51. What's more, its systematic name is 2-{2-[4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl]ethoxy}ethanol. Its classification codes are: (1)Antipsychotic Agents; (2)Central Nervous System Agents; (3)Central Nervous System Depressants; (4)Psychotropic Drugs; (5)Tranquilizing Agents. It is an atypical antipsychotic approved for the treatment of schizophrenia, and bipolar disorder. It is sometimes used off-label, often as an augmentation agent, to treat conditions such as obsessive-compulsive disorder, post-traumatic stress disorder, autism, alcoholism, Borderline Personality Disorder, depression, Tourette syndrome, and has been used by physicians as a sedative for those with sleep disorders or anxiety disorders.

Physical properties of Quetiapine are: (1)ACD/LogP: 1.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.89; (4)ACD/LogD (pH 7.4): 1.55; (5)ACD/BCF (pH 5.5): 1.92; (6)ACD/BCF (pH 7.4): 8.77; (7)ACD/KOC (pH 5.5): 35.73; (8)ACD/KOC (pH 7.4): 162.8; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 62.6 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 110.15 cm3; (15)Molar Volume: 301 cm3; (16)Polarizability: 43.66×10-24cm3; (17)Surface Tension: 51.9 dyne/cm; (18)Density: 1.27 g/cm3; (19)Flash Point: 290.4 °C; (20)Enthalpy of Vaporization: 88.18 kJ/mol; (21)Boiling Point: 556.5 °C at 760 mmHg; (22)Vapour Pressure: 3.22E-13 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: N\1=C(\c3c(Sc2c/1cccc2)cccc3)N4CCN(CCOCCO)CC4
(2)Std. InChI: InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2
(3)Std. InChIKey: URKOMYMAXPYINW-UHFFFAOYSA-N

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