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130-61-0

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130-61-0 Usage

Chemical Properties

Pale Yellow Solid

Originator

Mellaril,Sandoz,US,1959

Uses

Different sources of media describe the Uses of 130-61-0 differently. You can refer to the following data:
1. Thioridazine hydrochloride has been used as an intercalating agent for analyzing the integrity of double-stranded DNA (dsDNA) using square-wave voltammetry (SWV) techniques. Thioridazine hydrochloride has also been used as a positive control for the inhibition of hepatic enzyme cytochrome P4502D6 (CYP2D6) in human liver microsomes.
2. Dopamine receptor blocker; parent compound of sulforidazine and mesoridazine. Antipsychotic
3. Thioridazine HCl is a dopamine receptor blocker and antipsychotic. It is the parent compound of sulforidazine and mesoridazine. This compound has been reported to bind strongly to dopamine receptors on cancer stem cells and cause differentiation leaving normal cells alone (see Can. Chem. News 12 July/August 2012).

Manufacturing Process

N-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by condensing m-methylmercapto-aniline (BP 163° to 165°C/16 mm Hg) with the potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N- (m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating, and then distilling.9.87 parts of N-(m-methylmercapto-phenyl)-aniline are heated with 2.93 parts of sulfur and 0.15 part of powdered iodine for 15 minutes in a bath at about 160°C. Upon termination of the ensuing evolution of hydrogen sulfide, animal charcoal is added to the reaction mixture and recrystallization carried out first from 40 parts by volume of chlorobenzene, and then from 25 to 30 parts by volume of benzene at the boiling temperature. The obtained citronyellow 3-methylmercapto-phenothiazine has a MP of 138° to 140°C.17.82 parts of 2-methylmercapto-phenothiazine, 3.4 parts of finely pulverized sodamide and 80 parts by volume of absolute xylene are heated to boiling for two hours at a bath temperature of 180°C under a reflux condenser and while stirring the reaction mixture. Without interrupting the heating, a solution of 13.2 parts of 2-(N-methyl-piperidyl-2')-1chloro-ethane in 40 parts by volume of absolute xylene is then added dropwise in the course of 1 1/2 hours. After further heating for 3 hours, the reaction mixture is cooled and, after the addition of 5 parts of ammonium chloride, is shaken three times with water, using 25 parts by volume each time. The xylene solution is extracted once with 35 parts by volume of 3 normal acetic acid and then three times, each time with 15 parts by volume of the said acid, after which the acetic acid extract is washed with 60 parts by volume of ether and is then made phenolphthalein-alkaline by means of 25 parts by volume of concentrated aqueous caustic soda solution.The precipitated oily base is taken up in a total of 100 parts by volume of benzene. The benzene layer, dried over potassium carbonate, is filtered and then evaporated under reduced pressure. The residue from the evaporation is distilled in a high vacuum; after separating a preliminary distillate which passes over up to 228°C under a pressure of 0.92 mm Hg, the principal fraction, 2-methylmercapto-10-[2'-(N-methyl-piperidyl-2'')-ethyl- 1']phenothiazine, which distills over at 228° to 232°C under the lastmentioned pressure, is collected. The analytically pure base has a BP of 230°C/0.02 mm Hg.

Therapeutic Function

Tranquilizer

General Description

Thioridazine hydrochloride,10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)phenothiazine monohydrochloride (Mellaril), is amember of the piperidine subgroup of the phenothiazines.The drug has a relatively low tendency to produce EPS. Thedrug has high anticholinergic activity, and this activity in thestriatum, counterbalancing a striatal DA block, may be responsiblefor the low EPS. It also has been suggested thatthere may be increased DA receptor selectivity, which may be responsible. The drug has sedative and hypotensive activityin common with chlorpromazine and less antiemeticactivity. At high doses, pigmentary retinopathy has been observed.Its major metabolites include N-demethylated, ringhydroxylated,and S-oxidized products. Thioridazine isprominently converted to the active metabolite mesoridazine(discussed next), which probably contributes to the antipsychoticactivity of thioridazine.

Biological Activity

Dopamine receptor antagonist that displays antipsychotic activity.

Biochem/physiol Actions

D2 dopamine receptor antagonist; phenothazine antipsychotic with reduced extrapyramidal side effects; Ca2+ channel blocker.

Check Digit Verification of cas no

The CAS Registry Mumber 130-61-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 130-61:
(5*1)+(4*3)+(3*0)+(2*6)+(1*1)=30
30 % 10 = 0
So 130-61-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H26N2S2.ClH/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23;/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1H

130-61-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (T1300000)  Thioridazine hydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 130-61-0

  • T1300000

  • 1,880.19CNY

  • Detail

  • USP

  • (1663008)  Thioridazine hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 130-61-0

  • 1663008-200MG

  • 4,326.66CNY

  • Detail

  • Sigma

  • (T9025)  Thioridazine hydrochloride  ≥99%

  • 130-61-0

  • T9025-5G

  • 926.64CNY

  • Detail

  • Sigma

  • (T9025)  Thioridazine hydrochloride  ≥99%

  • 130-61-0

  • T9025-25G

  • 3,715.92CNY

  • Detail

130-61-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name thioridazine hydrochloride

1.2 Other means of identification

Product number -
Other names 10-[2-(1-Methyl-2-piperidyl)ethyl]-2-(methylthio)-10H-phenothiazine hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:130-61-0 SDS

130-61-0Synthetic route

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 18h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water		100%
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 50 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water
View Scheme
thioridazine
50-52-2, 52496-67-0, 57129-06-3, 114488-10-7

thioridazine

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water100%
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

chlorpromazine sulfoxide
969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide In water for 72h; Ambient temperature;93%
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

1-chloroethyl 2-(2-(2-(methylthio)-10hphenothiazin-10-yl)ethyl)piperidine-1-carboxylate

1-chloroethyl 2-(2-(2-(methylthio)-10hphenothiazin-10-yl)ethyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: thioridazine Hydrochloride With triethylamine In 1,2-dichloro-ethane at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane for 12h; Inert atmosphere; Reflux;		84%
1-methyl-1-propanethiol
513-53-1

1-methyl-1-propanethiol

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

2-(sec-butylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine
96457-89-5

2-(sec-butylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;71%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

2-(cyclohexylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

2-(cyclohexylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;62%
1-Adamantanethiol
34301-54-7

1-Adamantanethiol

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

2-((adamantan-1-yl)thio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

2-((adamantan-1-yl)thio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;61%
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

phenylmethanethiol
100-53-8

phenylmethanethiol

2-(benzylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine
97013-68-8

2-(benzylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;56%
1-Bromopentane
110-53-2

1-Bromopentane

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

1-methyl-2-(2-(2-(methylthio)-10H-phenothiazin-10-yl)ethyl)-1-pentylpiperidin-1-ium bromide

1-methyl-2-(2-(2-(methylthio)-10H-phenothiazin-10-yl)ethyl)-1-pentylpiperidin-1-ium bromide

Conditions
ConditionsYield
In acetonitrile for 24h; Reflux; Inert atmosphere;51%
Octanethiol
111-88-6

Octanethiol

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

10-(2-(1-methylpiperidin-2-yl)ethyl)-2-(octylthio)-10H-phenothiazine

10-(2-(1-methylpiperidin-2-yl)ethyl)-2-(octylthio)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;49%
zinc acetate hydrate

zinc acetate hydrate

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

ZnC6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3)Cl(2+)*2CH3COO(1-)=[ZnC6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3)Cl](CH3COO)2

ZnC6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3)Cl(2+)*2CH3COO(1-)=[ZnC6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3)Cl](CH3COO)2

Conditions
ConditionsYield
In methanol slow addn. of soln. of ZnCl2 to soln. of ligand (room temp.), stirring (1 h), conctg. (reduced pressure), storing (overnight at 4°C); decanting viscous liq., redissolving in methanol with stirring at 60°C, suction filtn., washing (2-3 times, cold methanol), drying (air),drying (vac.), recrystn. (hot methanol), elem. anal.;48.5%
(1R,2S,5R)-menthyl chloroformate
14602-86-9

(1R,2S,5R)-menthyl chloroformate

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

A

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{(2S)-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{(2S)-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

B

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{(2R)-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{(2R)-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;A 43%
B 38%
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

Zn(C6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3))2Cl2(2+)*2Cl(1-)*CH3OH=[Zn(C6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3))2Cl2]Cl2*CH3OH

Zn(C6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3))2Cl2(2+)*2Cl(1-)*CH3OH=[Zn(C6H4SN((CH2)2C5H9NHCH3)C6H3(SCH3))2Cl2]Cl2*CH3OH

Conditions
ConditionsYield
In methanol slow addn. of soln. of ZnCl2 to soln. of ligand (room temp.), refluxing (60°C, 1.5-2 h), cooling (overnight to 4°C); decanting oily product, redissolving in methanol with stirring at 60°C, suction filtn., washing (2-3 times, cold methanol), drying (air),drying (vac.), recrystn. (hot methanol), elem. anal.;35.1%
hydrogenchloride
7647-01-0

hydrogenchloride

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

palladium dichloride

palladium dichloride

((C6H4)(C6H3SCH3)N(CH2CH2C5H9NHCH3)S)Pd2Cl5*2H2O

((C6H4)(C6H3SCH3)N(CH2CH2C5H9NHCH3)S)Pd2Cl5*2H2O

Conditions
ConditionsYield
In methanol dissolving ligand in methanol, slow addn. with stirring to conctd. methanolic soln. of PdCl2 contg. HCl (room temp.), stirring (1 h), cooling (overnight to 4°C); suction filtn., washing (several times, cold water, cold methanol), air drying, drying in vac. over anhydrous CaSO4, recrystn. from hot methanol, elem. anal.;30%
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

C21H27N2S2

C21H27N2S2

Conditions
ConditionsYield
With potassium metaperiodate; phosphoric acid; sulfuric acid In water
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Thioridazine 5-sulfoxide
7776-05-8

Thioridazine 5-sulfoxide

Conditions
ConditionsYield
With potassium dichromate In water at 25℃; for 1h;
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

thioridazine cation-radical

thioridazine cation-radical

Conditions
ConditionsYield
With iron(III) chloride In water at 25℃; Product distribution; Further Variations:; Temperatures; Reagents;
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Pt(C6H4SN(CH2CH2C5H9NH(CH3))C6H3SCH3)Cl3
82489-48-3

Pt(C6H4SN(CH2CH2C5H9NH(CH3))C6H3SCH3)Cl3

Conditions
ConditionsYield
In water byproducts: KCl; aq. soln. of ligand mixed with Pt complex; filtered off, washed with H2O, dried in vac. at 100 °C; elem. anal.;
potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Pd(C6H4SN(CH2CH2C5H9NH(CH3))C6H3SCH3)Cl3
82489-46-1

Pd(C6H4SN(CH2CH2C5H9NH(CH3))C6H3SCH3)Cl3

Conditions
ConditionsYield
In water byproducts: KCl; aq. soln. of ligand mixed with Pd complex; filtered off, washed with H2O, dried in vac. at 100 °C; elem. anal.;
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

Northioridazine
10538-32-6, 114991-17-2, 114991-18-3

Northioridazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / 1,2-dichloro-ethane / 0.33 h / 20 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere; Reflux
2.1: water / methanol / 12 h / Reflux; Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

10-(2-(1-benzylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine

10-(2-(1-benzylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / 1,2-dichloro-ethane / 0.33 h / 20 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere; Reflux
2.1: water / methanol / 12 h / Reflux; Inert atmosphere
3.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
3.2: 24 h / 20 °C / Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

2-(methylthio)-10-(2-(1-propylpiperidin-2-yl)ethyl)-10H-phenothiazine

2-(methylthio)-10-(2-(1-propylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / 1,2-dichloro-ethane / 0.33 h / 20 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere; Reflux
2.1: water / methanol / 12 h / Reflux; Inert atmosphere
3.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
3.2: 24 h / 20 °C / Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

10-(2-(1-isopropylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine

10-(2-(1-isopropylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / 1,2-dichloro-ethane / 0.33 h / 20 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere; Reflux
2.1: water / methanol / 12 h / Reflux; Inert atmosphere
3.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
3.2: 24 h / 20 °C / Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

(+)-Thioridazine

(+)-Thioridazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

(-)-Thioridazine

(-)-Thioridazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

(R)-northioridazine

(R)-northioridazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
3.1: carbonochloridic acid 1-chloro-ethyl ester; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.2: 4 h / Reflux; Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

(R)-nosyl-northioridazine

(R)-nosyl-northioridazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2: chlorotriisopropylsilane; trifluoroacetic acid / water / 72 h / 110 °C / Sealed tube
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
3.1: carbonochloridic acid 1-chloro-ethyl ester; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.2: 4 h / Reflux; Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

C50H51Cl2N9O6S3

C50H51Cl2N9O6S3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: chlorotriisopropylsilane; trifluoroacetic acid / water / 72 h / 110 °C / Sealed tube
3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
3.2: 16 h / 20 °C
4.1: water; tert-butyl alcohol / 20 °C
4.2: 33 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
3.1: carbonochloridic acid 1-chloro-ethyl ester; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.2: 4 h / Reflux; Inert atmosphere
4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
4.2: 16 h / 20 °C
5.1: water; tert-butyl alcohol / 20 °C
5.2: 33 °C
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

C49H49Cl2N9O6S3

C49H49Cl2N9O6S3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: chlorotriisopropylsilane; trifluoroacetic acid / water / 72 h / 110 °C / Sealed tube
3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
3.2: 16 h / 20 °C
4.1: water; tert-butyl alcohol / 20 °C
4.2: 58 h / 33 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
3.1: carbonochloridic acid 1-chloro-ethyl ester; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.2: 4 h / Reflux; Inert atmosphere
4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
4.2: 16 h / 20 °C
5.1: water; tert-butyl alcohol / 20 °C
5.2: 58 h / 33 °C
View Scheme
thioridazine Hydrochloride
130-61-0

thioridazine Hydrochloride

C49H49Cl2N9O6S3

C49H49Cl2N9O6S3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: chlorotriisopropylsilane; trifluoroacetic acid / water / 72 h / 110 °C / Sealed tube
3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
3.2: 16 h / 20 °C
4.1: water; tert-butyl alcohol / 20 °C
4.2: 58 h / 33 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 20 °C / Reflux; Inert atmosphere
3.1: carbonochloridic acid 1-chloro-ethyl ester; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3.2: 4 h / Reflux; Inert atmosphere
4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
4.2: 16 h / 20 °C
5.1: water; tert-butyl alcohol / 20 °C
5.2: 58 h / 33 °C
View Scheme

130-61-0Upstream product

130-61-0Relevant articles and documents

THE (S)-ENANTIOMER OF MEPAZINE

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Page/Page column 47; 49; 50, (2015/01/16)

The present invention relates to the (S)-enantiomer of mepazine, its applicability in therapy, a pharmacological composition comprising (S)-mepazine, and processes for the preparation of (S)- mepazine and one of its intermediates.

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