2622-26-6

Basic information

• Product Name: PROPERICYAZINE
• Synonyms: PROPERICIAZINE;PROPERICYAZINE;1-(3-(2-cyano-10-phenothiazinyl)propyl)-4-piperidino;10-(3-(4-hydroxypiperidino)propyl)-phenothiazine-2-carbonitril;10-(3-(4-Hydroxypiperidino)propyl)phenothiazine-2-carbonitrile;10-[3-(4-Hydroxy-1-piperidinyl)propyl]-10H-phenothiazine-2-carbonitrile;10H-Phenothiazine-2-carbonitrile, 10-[3-(4-hydroxy-1-piperidinyl)propyl]-;2-Cyano-10-(3-(4-hydroxy-1-piperidyl)propyl)phenothiazine
• CAS NO: 2622-26-6
• Molecular Formula: C₂₁H₂₃N₃OS
• Molecular Weight: 365.49
• EINECS: 220-071-3
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;AOLEPT
• Mol File: 2622-26-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 116-117°
• Boiling Point: 593.4°Cat760mmHg
• Flash Point: 312.7°C
• Appearance: /
• Density: 1.1198 (rough estimate)
• Vapor Pressure: 6.29E-15mmHg at 25°C
• Refractive Index: 1.6740 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.87±0.20(Predicted)
• Water Solubility: 38.01mg/L(37 oC)
• CAS DataBase Reference: PROPERICYAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPERICYAZINE(2622-26-6)
• EPA Substance Registry System: PROPERICYAZINE(2622-26-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36
• RTECS: SN7175000
• Hazardous Substances Data: 2622-26-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Originator

Aolept, Bayer Vital

Uses

Different sources of media describe the Uses of 2622-26-6 differently. You can refer to the following data:
1. Psychotherapeutic phenothiazine. Antipsychotic.
2. Spectrophotometric reagent for palladium and ruthenium.

Definition

ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine substituted by a 3-(4-hydroxypiperidin-1-yl)propyl group at the nitrogen atom and a carbonitrile group at position 2. Periciazine is a first generation antipsychotic.

Manufacturing Process

2-Cyano-10-(3-methanesulfonyloxypropyl)phenthiazine and 4hydroxypiperidine in toluene were heated under reflux with stirring. The reaction mixture was allowed to cool and water was added. The resulting toluene solution layer was decanted and washed twice with water. The toluene solution was then stirred with 5% hydrochloric acid. The hydrochloride of the desired phenthiazine base precipitated in gummy condition in the aqueous layer. This was decanted and treated with sodium hydroxide (density 1.33). It was then extracted three times with ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated in vacuum. A resinous product was obtained. This product was dissolved in a mixture of benzene and cyclohexane and chromatographed on a column containing alumina. The chromatographed product was eluted successively with mixtures of benzene and cyclohexane and then with benzene and finally with a mixture of benzene and ethyl acetate. The eluates were evaporated to yield a crude product. This product was recrystallised from aqueous ethanol (40% water) and yielded 2cyano-10-[3-(4-hydroxy-1-piperidyl)propyl]phenthiazine as white crystals.

Therapeutic Function

Neuroleptic

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Used as an antipsychotic agent. When heated to decomposition it emits very toxic fumes of CN-, NOx, and SOx. See also NITRILES.

Purification Methods

It recrystallises from a saturated solution in cyclohexane. It is antipsychotic and is a sensitive reagent for Pd, Va, Ru, Rh and Au. [Gowda et al. Anal Chem 55 1816 1983, Anal Chim Acta 154 347 1983, Beilstein 27 III/IV 4110.]

InChI:InChI=1/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2

Synthetic route

4-HYDROXYPIPERIDINE (5382-16-1) + 10H-phenothiazine-2-carbonitrile (38642-74-9) + 1,3-chlorobromopropane (109-70-6) → periciazine (2622-26-6)

Conditions	Yield
Stage #1: 10H-phenothiazine-2-carbonitrile; 1.3-chlorobromopropane With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 7h; Stage #2: 4-HYDROXYPIPERIDINE With triethylamine In N,N-dimethyl-formamide at 0 - 60℃; for 42h;	40%

periciazine (2622-26-6) → 10-(3-(4-oxopiperidin-1-yl)propyl)-10H-phenothiazine-2-carbonitrile (96265-39-3)

Conditions	Yield
With dmap; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; copper(l) chloride In acetonitrile at 20℃; for 1h; chemoselective reaction;	97%

yttrium(III) nitrate (13494-98-9) + periciazine (2622-26-6) → Y(3+)*2C21H23N3OS*3NO3(1-) = [Y(C21H23N3OS)2(NO3)2](NO3)

Conditions	Yield
In ethanol 15 min; pptn. washing (EtOH), drying (vac.); elem. anal.;	74%

uranyl(VI) acetate dihydrate + periciazine (2622-26-6) → UO2(CH3CO2)2(C6H4SN((CH2)3NC5H9OH)C6H3CN)(H2O)2

Conditions	Yield
In water soln. refluxed for 6 h; cooling under ice-cold water for 4 d; ppt. filtered and dried in vac.; elem. anal.;	50%

zirconium(IV) nitrate + periciazine (2622-26-6) → Zr(NO3)4 (propericiazine)

Conditions	Yield
In sulfuric acid; water aq. H2SO4; stirring (soln. of Zr(NO3)4 in water), addn. (soln. of ligand in water, sulphuric acid), pptn., set aside (2 h); sepn. (filtration), washing (water, EtOH), drying (vac., over fused CaCl2); elem. anal.;

rhodium(III) chloride trihydrate + periciazine (2622-26-6) → rhodium (II,III) (propericiazine)2 Cl8

Conditions	Yield
In ethanol addn. of ethanolic soln. of PPC to a constantly stirred ethanolic soln. of RhCl3*3H2O at room temp., pptn.; filtration, washing with ethanol and ether, drying in vac. over fused CaCl2, elem. anal.;

ruthenium(III) chloride trihydrate + periciazine (2622-26-6) → Ru3(C6H4SN(C3H6N(C5H9OH))C6H3(CN))2Cl8

Conditions	Yield
In ethanol addn. of ethanolic N-alkylphenothiazine soln. to ethanolic RuCl3*3H2O soln., stirring slowly; filtration; washing (ethanol, ether, several times); drying (anhydrous CaCl2, desiccator); elem. anal.;

sodium tungstate (VI) dihydrate (10213-10-2) + periciazine (2622-26-6) → W2O4(C6H4SN((CH2)3NC5H9OH)C6H3CN)2(H2O)2

Conditions	Yield
With HCl In water a soln. of Na2WO4*2H2O in distd. H2O was added with stirring to a soln.of PPC in distd. H2O containing few drops of 2 M HCl; the suspn. was set aside for 3 h, filtered, washed (H2O, EtOH), dried in vac. over fused CaCl2; elem. anal.;

hexaammonium heptamolybdate tetrahydrate + periciazine (2622-26-6) → Mo2O4(C6H4SN(CH2)3NC5H9OHC6H3CN)2(H2O)2

Conditions	Yield
In hydrogenchloride (NH4)6Mo7O24*4H2O in 2 M HCl was added to soln. of ligand in water with vigorous stirring, suspn. set aside for 2 h; suspn. filtered, washed with water, ethanol and dried in vacuo over fused CaCl2; elem. anal.;	67-79

Upstream product

• 5382-16-1 4-HYDROXYPIPERIDINE 
• 38642-74-9 10H-phenothiazine-2-carbonitrile 
• 109-70-6 1.3-chlorobromopropane 

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