132-18-3

Basic information

• Product Name: 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE
• Synonyms: 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE;4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE MONOHYDRATE;4-BENZHYDRYLOXY-1-METHYL PIPERIDINE HCL;LABOTEST-BB LT00159897;DIPHENYLPYRALINE HCL;DIPHENYLPYRALINE HYDROCHLORIDE;4-Benzhydryloxy-1-methylpiperidine~Diphenylpyraline hydrochloride;4-diphenylmethoxy-1-methylpiperidine hydrochlorid
• CAS NO: 132-18-3
• Molecular Formula: C₁₉H₂₄NO*Cl
• Molecular Weight: 317.85
• EINECS: 205-049-3
• Product Categories: API intermediates;API
• Mol File: 132-18-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 203-205 °C(lit.)
• Boiling Point: 378.7°Cat760mmHg
• Flash Point: 111.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 6.18E-06mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• Merck: 13,3363
• CAS DataBase Reference: 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE(132-18-3)
• EPA Substance Registry System: 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE HYDROCHLORIDE(132-18-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: TM7823600
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 132-18-3(Hazardous Substances Data)

Usage

Description

Diphenylpyraline is an antihistamine drug with anticholinergic and sedative action. It is intended for symptomatic treatment of seasonal allergies and allergic reactions as well as an adjuvant drug in anaphylactic reaction therapy. Synonyms of this drug are arbid, timpil, histryl, hispril, and others.

Originator

Diafen,Riker,US,1955

Uses

Different sources of media describe the Uses of 132-18-3 differently. You can refer to the following data:
1. Antihistaminic;H1 antagonist
2. Diphenylpyraline Hydrochloride is a salt of Diphenylpyraline (D492110), an H1 receptor antagonist (an antihistamine) and is commonly prescribed to treat allergic and vasomotor rhinitis. There is also some research being conducted on diphenylpyraline derivatives to determine their antimycobacterial and antifungal activity.

Definition

ChEBI: The hydrochloride salt of diphenylpyraline. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders.

Manufacturing Process

A mixture of 46 grams of 1-methyl-4-piperidinol (0.4 mol), 49.4 grams of benzhydryl omide (0.2 mol) and 100 ml of xylene was refluxed for approximately 24 hours. The reaction mixture separated into two phases with the upper phase containing the desired ether compound dissolved in xylene. The lower phase consisted of the hydroomide salt of the excess 1-methyl-4- piperidinol. The upper phase was separated from the lower phase and the desired benzhydryl ether recovered in the crude state by distilling off the xylene under reduced pressure. The crude benzhydryl ether was a clear reddish oil. It was dissolved in 75 ml of 20% hydrochloric acid and the aqueous acid solution then washed three times with 50 ml portions each of ethyl ether. The aqueous acid solution was then decolorized with activated carbon and thereafter slowly admixed with 75 ml of 28% aqueous ammonia. The benzhydryl ether separated as an oily material and was removed from the aqueous mixture by extraction with three 50 ml portions of ethyl ether.On evaporation of the ethyl ether from the ethyl ether solution, the benzhydryl ether was recovered as a pale yellow oil. The benzhydryl ether was dissolved in 60 ml of isopropanol and the isopropanol solution acidified to a pH of 3 with dry hydrogen chloride-methanol solution. The acidic propanol solution was then diluted with ethyl ether until a faint turbidity was observed. In a short time, the crystalline hydrochloride salt of the benzhydryl ether separated from the propanol solution. The crystallized salt was recrystallized once from 75 ml of isopropanol with the aid of ethyl ether in order to further purify the material. A yield of the pure hydrochloride salt of 1-methylpiperidyl- 4-benzhydryl ether of 24.5 grams was obtained. This was 39% of the theoretical yield. The pure material had a melting point of 206°C.

Therapeutic Function

Antihistaminic

General Description

Diphenylpyr alinehydrochloride, 4-(diphenylmethoxy)-1-methylpiperidinehydrochloride (Hispril, Diafen) is a white or slightly offwhitecrystalline powder that is soluble in water or alcohol.Diphenylpyraline is structurally related to diphenhydraminewith the aminoalkyl side chain incorporated in a piperidinering. It is a potent antihistaminic, and the usual dose is 2 mg3 or 4 times daily.

Synthesis

Diphenylpyraline, 4-diphenylmethoxy-1-methylpiperidine (16.1.32), is synthesized by alkylating 4-hydroxy-1-methylpiperidine with benzhydrylbromide.

InChI:InChI=1/C19H23NO.ClH/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17;/h2-11,18-19H,12-15H2,1H3;1H

Synthetic route

cobalt(II) chloride hexahydrate + diphenylpyraline hydrochloride (132-18-3) → {Co(CH3NC5H9OCH(C6H5)2)2(H2O)2Cl2} (145519-05-7)

Conditions	Yield
In ethanol addn. of soln. of diphenyl pyraline hydrochloride (0.02 mol) in ethanol to soln. of CoCl2*6H2O (0.01 mol) in ethanol; keeping at room temp. for 10 min, then warming to 60°C for 30 min (water bath);; pptn.; filtering, washing with cold ethanol and with ether, drying over P4O10; elem. anal.;;	82%

diphenylpyraline hydrochloride (132-18-3) + copper(II) nitrate → Cu(C19H23NO)2(NO3)2 (203715-86-0)

Conditions	Yield
In ethanol byproducts: HCl; stirring (60-70°C, 0.5-10.0 h); pptn. on cooling, washing (EtOH), drying; elem. anal.;	82%

diphenylpyraline hydrochloride (132-18-3) + copper dichloride → Cu(C19H23NO)2Cl2 (203715-85-9)

Conditions	Yield
In ethanol byproducts: HCl; stirring (60-70°C, 0.5-10.0 h); pptn. on cooling, washing (EtOH), drying; elem. anal.;	80%

diphenylpyraline hydrochloride (132-18-3) + copper(II) perchlorate → Cu(C19H23NO)2(ClO4)2 (203715-88-2)

Conditions	Yield
In ethanol byproducts: HCl; stirring (60-70°C, 0.5-10.0 h); pptn. on cooling, washing (EtOH), drying; elem. anal.;	74%

cobalt(II) diacetate tetrahydrate (6147-53-1) + diphenylpyraline hydrochloride (132-18-3) → {Co(CH3NC5H9OCH(C6H5)2)2(H2O)2(CH3CO2)2} (145519-09-1)

Conditions	Yield
In ethanol addn. of soln. of diphenyl pyraline hydrochloride (0.02 mol) in ethanol to soln. of Co(CH3CO2)2*4H2O (0.01 mol) in ethanol; stirring vigorously at room temp. for 30 min;; pptn.; filtering, washing with cold ethanol and with ether, drying on air; elem. anal.;;	68%

cobalt(II) nitrate hexahydrate + diphenylpyraline hydrochloride (132-18-3) → {Co(CH3NC5H9OCH(C6H5)2)2(H2O)2(NO3)2} (145519-06-8)

Conditions	Yield
In ethanol addn. of soln. of diphenyl pyraline hydrochloride (0.02 mol) in ethanol to soln. of Co(NO3)2*6H2O (0.01 mol) in ethanol; stirring vigorously at room temp. for 30 min;; pptn.; filtering, washing with cold ethanol and with ether, drying on air; elem. anal.;;	67%

cobalt(II) perchlorate + diphenylpyraline hydrochloride (132-18-3) → {Co(CH3NC5H9OCH(C6H5)2)2(H2O)2(ClO4)2} (145519-08-0)

Conditions	Yield
In ethanol addn. of soln. of diphenyl pyraline hydrochloride (0.02 mol) in ethanol to soln. of Co(ClO4)2 (0.01 mol) in ethanol; stirring vigorously at room temp. for 30 min;; pptn.; filtering, washing with cold ethanol and with ether, drying on air; elem. anal.;;	62%

copper diacetate (142-71-2) + diphenylpyraline hydrochloride (132-18-3) → Cu(C19H23NO)2(CH3COO)2 (203715-87-1)

Conditions	Yield
In ethanol byproducts: HCl; stirring (60-70°C, 0.5-10.0 h); pptn. on cooling, washing (EtOH), drying; elem. anal.;	57%

cobalt(II) sulphate heptahydrate + diphenylpyraline hydrochloride (132-18-3) → Co(2+)*2CH3NC5H9OCH(C6H5)2*2H2O*SO4(2-)={Co(CH3NC5H9OCH(C6H5)2)2(H2O)2(SO4)}

Conditions	Yield
In ethanol addn. of soln. of diphenyl pyraline hydrochloride (0.02 mol) in ethanol to soln. of CoSO4*7H2O (0.01 mol) in ethanol; keeping at room temp. for 10 min, then warming to 60°C for 30 min (water bath);; pptn.; filtering, washing with cold ethanol and with ether, drying over P4O10; elem. anal.;;	41%

Downstream Products

• 203715-85-9 Cu(C₁₉H₂₃NO)2Cl₂ 
• 203715-87-1 Cu(C₁₉H₂₃NO)2(CH₃COO)2 
• 203715-86-0 Cu(C₁₉H₂₃NO)2(NO₃)2 
• 145519-06-8 {Co(CH₃NC₅H₉OCH(C₆H₅)2)2(H₂O)2(NO₃)2} 
• 145519-05-7 {Co(CH₃NC₅H₉OCH(C₆H₅)2)2(H₂O)2Cl₂} 
• 145519-08-0 {Co(CH₃NC₅H₉OCH(C₆H₅)2)2(H₂O)2(ClO₄)2} 
• 145519-09-1 {Co(CH₃NC₅H₉OCH(C₆H₅)2)2(H₂O)2(CH₃CO₂)2}