Quetiapine supplier | CasNO.111974-69-7

Name
2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol
EINECS
CAS No. 111974-69-7
Article Data43
CAS DataBase
Density 1.27 g/cm³
Solubility
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
Appearance white crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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]-;
PSA 73.60000
LogP 2.16740

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

: 870676-47-4
C6H10O4

: 5747-48-8
11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine

: 111974-69-7
Quetiapine

Conditions

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

: 11-[4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f][1,4]thiazepine hemifumarate salt

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 1.5h;
With sodium hydroxide In dichloromethane; water at 20℃; for 1.5h;
With ammonium hydroxide In water pH=9;	170 mg

: N-Dealkyl Quetiapine dihydrochloride

: 628-89-7
2-(2-Chloroethoxy)ethanol

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
With sodium carbonate; sodium iodide In water at 100 - 105℃; for 9h; Product distribution / selectivity;
Stage #1: N-Dealkyl Quetiapine dihydrochloride; 2-(2-Chloroethoxy)ethanol Stage #2: With 1-methyl-2-pyrrolidine; sodium carbonate; sodium iodide In toluene Further stages.;

: 11-[4-(2-methanesulphonylethyl)-1-piperazinyI]dibenzo[b,f][1,4]thiazepine

: 107-21-1
ethylene glycol

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
With sodium hydride In toluene for 10 - 12h; Product distribution / selectivity; Heating / reflux;

: 5747-48-8
11-(1-piperazinyl)dibenzo[b,f][1,4]thiazepine

: 1643-19-2
tetrabutylammomium bromide

: 628-89-7
2-(2-Chloroethoxy)ethanol

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
With sodium carbonate In water; toluene
With sodium carbonate In water; toluene
With sodium carbonate In water; toluene

...Expand

: 13349-82-1
1-[2-(2-hydroxyethoxy)ethyl]piperazine

: 1176987-11-3
dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
Stage #1: 1-[2-(2-hydroxyethoxy)ethyl]piperazine; dibenzo[b,f][1,4]thiazepin-11-ylamine hydrochloride With N,N-dimethyl-cyclohexanamine at 155℃; for 58h; Stage #2: With hydrogenchloride In dichloromethane; water for 1.5h; Heating / reflux; Stage #3: With sodium hydroxide In water pH=13 - 14;

: 13745-86-3
11-chloro-dibenzo[b,f][1,4]thiazepine

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

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
With potassium carbonate In sulfolane at 95 - 100℃; for 4h;
Stage #1: 11-chloro-dibenzo[b,f][1,4]thiazepine; 1-[2-(2-hydroxyethoxy)ethyl]piperazine hydrochloride With sodium carbonate; sodium iodide In toluene at 20℃; for 12h; Reflux; Stage #2: With (2E)-but-2-enedioic acid In isopropyl alcohol for 1h; Reflux;

: 19806-43-0
2‑(2‑nitrophenylsulfanyl)benzoic acid

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 40 °C 1.2: 0 - 5 °C 2.1: formic acid; iron / 85 - 90 °C View Scheme

: 147-93-3
Thiosalicylic acid

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; isopropyl alcohol / Inert atmosphere; Reflux 2.1: thionyl chloride / dichloromethane / 40 °C 2.2: 0 - 5 °C 3.1: formic acid; iron / 85 - 90 °C View Scheme

: 88-73-3
2-Chloronitrobenzene

: 111974-69-7
Quetiapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; isopropyl alcohol / Inert atmosphere; Reflux 2.1: thionyl chloride / dichloromethane / 40 °C 2.2: 0 - 5 °C 3.1: formic acid; iron / 85 - 90 °C View Scheme

: 110-17-8
(2E)-but-2-enedioic acid

: 111974-69-7
Quetiapine

: 111974-72-2
quetiapine fumarate

Conditions

Conditions	Yield
In ethyl acetate; toluene at 20℃; for 1.08333h; Product distribution / selectivity; Heating / reflux;	99%
Stage #1: Quetiapine With pyrographite In methanol for 0.5h; Reflux; Stage #2: (2E)-but-2-enedioic acid at 40℃; pH=4 - 5;	98%
In methanol at 10 - 25℃; for 1.58333h; Heating / reflux;	94%

: 111974-69-7
Quetiapine

: quetiapine N19-oxide

Conditions

Conditions	Yield
Stage #1: Quetiapine With 3-chloro-benzenecarboperoxoic acid In chloroform at 23℃; for 0.166667h; Inert atmosphere; Stage #2: With triethylamine In chloroform for 0.166667h; Inert atmosphere;	97%

: 110-17-8
(2E)-but-2-enedioic acid

: 111974-69-7
Quetiapine

: 11-[4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f][1,4]thiazepine hemifumarate salt

Conditions

Conditions	Yield
In ethanol at 30 - 85℃; for 2.5h;	96.4%
With sulfuric acid In ethanol at 20℃; for 8h;	94%
In acetone at 20℃;
In methanol at 70 - 75℃; for 0.5h;
Stage #1: (2E)-but-2-enedioic acid; Quetiapine In methanol at 5 - 65℃; for 5.5h; Stage #2: (2E)-but-2-enedioic acid In methanol at 60℃; Product distribution / selectivity;

: 2,3-O-isopropylidene-4-O-benzyl-α-L-rhamnopyranosyl diphenylphosphate

: 111974-69-7
Quetiapine

A: C37H45N3O6S

B: C37H45N3O6S

Conditions

Conditions	Yield
With C53H57F11N6O4S2 In di-isopropyl ether at 50℃; for 48h; Molecular sieve; Sealed tube; Overall yield = 76 percent; Overall yield = 0.075 g; stereoselective reaction;	A n/a B 96%

...Expand

: 3392-12-9
Boc-Val-ONSu

: 111974-69-7
Quetiapine

: 1314005-85-0
Boc-Val-QTP

Conditions

Conditions	Yield
Stage #1: Quetiapine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.5h; Stage #2: Boc-Val-ONSu In tetrahydrofuran for 1h; Stage #3: With ammonium chloride In tetrahydrofuran; water for 0.25h;	95%

: 110-17-8
(2E)-but-2-enedioic acid

: 111974-69-7
Quetiapine

: quetiapine fumarate

Conditions

Conditions	Yield
In methanol; ethanol at 40 - 45℃;	93.3%
In ethanol Reflux;	79%
In isopropyl alcohol at 80 - 85℃; for 1.5h;
Stage #1: Quetiapine With pyrographite In butan-1-ol at 60 - 70℃; for 1.5h; Stage #2: (2E)-but-2-enedioic acid In butan-1-ol at 20 - 60℃; for 2.5 - 3h; Product distribution / selectivity;
In isopropyl alcohol for 1h; Heating / reflux;

: 144-62-7
oxalic acid

: 111974-69-7
Quetiapine

: quetiapine oxalate

Conditions

Conditions	Yield
In acetone; toluene at 25℃; for 1.08333h; Heating / reflux;	89%
In ethanol at 0 - 20℃; for 4h; Heating / reflux;

: 111974-69-7
Quetiapine

: quetiapine N19,S-dioxide

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 23℃; for 18h; Cooling with ice; Inert atmosphere;	87%
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.17 h / 23 °C / Inert atmosphere 1.2: 0.17 h / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.17 h / 23 °C / Inert atmosphere 2.2: 0.17 h / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.17 h / 23 °C / Inert atmosphere 1.2: 0.17 h / Inert atmosphere 2.1: osmium(VIII) oxide / water; tert-butyl alcohol / 19 h / 20 °C / Inert atmosphere View Scheme

: 107-13-1
acrylonitrile

: 111974-69-7
Quetiapine

: 1606176-56-0
3-(2-(2-(4-(dibenzo[b,f]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethoxy)propanenitrile

Conditions

Conditions	Yield
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; benzylamine; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 4℃; for 1h; Inert atmosphere; chemoselective reaction;	84%

: Phosphoric acid diphenyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

: 111974-69-7
Quetiapine

: C55H59N3O7S

Conditions

Conditions	Yield
With (S)-4-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-5-((R)-2-(4-fluorophenyl)-2-methylpyrrolidin-1-yl)-3,3-dimethyl-5-oxopentyl 3-(3-((S)-1-((R)-2-(4-fluorophenyl)-2-methylpyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)thioureido)-5-(trifluoromethyl)benzoate In di-isopropyl ether at 40℃; for 19h; Molecular sieve; Sealed tube; stereoselective reaction;	72%

: 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl diphenylphosphate

: 111974-69-7
Quetiapine

: 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol-(2,3:4,6-di-O-isopropylidene-β-D-mannopyranose)

Conditions

Conditions	Yield
With C53H57F11N6O4S2 In di-isopropyl ether at 50℃; for 48h; Molecular sieve; Sealed tube; stereoselective reaction;	63%

: 7693-46-1
4-Nitrophenyl chloroformate

: 111974-69-7
Quetiapine

: C28H28N4O6S

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 22℃; for 20h; Inert atmosphere;	32%

: 111974-69-7
Quetiapine

: quetiapine fumarate

Conditions

Conditions	Yield
With (2E)-but-2-enedioic acid In acetone at 20 - 25℃; for 1h;
With (2E)-but-2-enedioic acid In ethyl acetate at 20 - 25℃; for 1h;
With (2E)-but-2-enedioic acid In tert-butyl methyl ether for 1.25h; Heating / reflux;

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

Product Name

2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol

Synthetic route

Quetiapine History

Quetiapine Specification

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