147-20-6

Basic information

• Product Name: diphenylpyraline
• Synonyms: benzhydryl 1-methyl-4-piperidyl ether;Belfene;Dayfen;Hispril;Hystryl;Mepiben;P-253;132-18-3 (Hcl)
• CAS NO: 147-20-6
• Molecular Formula: C₁₉H₂₃NO
• Molecular Weight: 281.39202
• EINECS: 205-686-7
• Mol File: 147-20-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 424.06°C (rough estimate)
• Flash Point: 111.6 °C
• Appearance: /
• Density: 1.0423 (rough estimate)
• Vapor Pressure: 6.18E-06mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: diphenylpyraline(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylpyraline(147-20-6)
• EPA Substance Registry System: diphenylpyraline(147-20-6)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 147-20-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of piperidines that is the benzhydryl ether derivative of 1-methyl-4-hydroxypiperidine. 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. It is also used as the teoclate salt (piprinhydrinate) as an ingredient in compound preparations for the symptomatic relief of coughs and the common cold.

Therapeutic Function

Antihistaminic

InChI:InChI=1/C19H23NO/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

Synthetic route

N-methyl-4-hydroxypiperidine (106-52-5) + diphenylchloromethane (90-99-3) → diphenylpyraline (147-20-6)

Conditions	Yield
With tributyl-amine; 4-methyl-2-pentanone

N-methyl-4-hydroxypiperidine (106-52-5) + Bromodiphenylmethane (776-74-9) → diphenylpyraline (147-20-6)

Conditions	Yield
With benzene Erhitzen des Reaktionsprodukts auf ca. 150grad;
With tributyl-amine; 4-methyl-2-pentanone

N-methyl-4-hydroxypiperidine (106-52-5) + diazodiphenylmethane (908093-98-1) → diphenylpyraline (147-20-6)

Conditions	Yield
With benzene

4-HYDROXYPIPERIDINE (5382-16-1) → diphenylpyraline (147-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / Reflux; Dean-Stark View Scheme

N-methyl-4-hydroxypiperidine (106-52-5) + 1,1-Diphenylmethanol (91-01-0) → diphenylpyraline (147-20-6)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene Reflux; Dean-Stark;

diphenylpyraline (147-20-6) + chloroformic acid ethyl ester (541-41-3) → ethyl 4-(diphenylmethoxy)-1-piperidinecarboxylate (65214-84-8)

Conditions	Yield
In toluene for 5.5h; Heating;	87%

diphenylpyraline (147-20-6) → 4-diphenylmethoxypiperidine (58258-01-8)

Conditions	Yield
With ethanol; sodium perchlorate; water for 12h; Reagent/catalyst; Electrochemical reaction; Green chemistry;	44%
Multi-step reaction with 2 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating View Scheme

diphenylpyraline (147-20-6) → ethyl 4-(4-benzhydryloxypiperidino)butanoate (125602-76-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C View Scheme

diphenylpyraline (147-20-6) → 4-(4-Benzhydryloxy-piperidin-1-yl)-butyric acid (133993-23-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C 4: 2N aq. NaOH / methanol / Heating View Scheme

diphenylpyraline (147-20-6) → ethyl <(4-diphenylmethoxy)piperidino>acetate (133015-42-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: 70 percent / K2CO3 / dimethylformamide / 2 h / 80 °C View Scheme

diphenylpyraline (147-20-6) → <4-(diphenylmethoxy)piperidino>acetic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: 70 percent / K2CO3 / dimethylformamide / 2 h / 80 °C 4: 2N aq. NaOH / methanol / 1 h / Heating View Scheme

diphenylpyraline (147-20-6) → 4-(diphenylmethoxy)-1-piperidinepropionic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C 4: 2N aq. NaOH / methanol / Heating View Scheme

diphenylpyraline (147-20-6) → 5-(4-Benzhydryloxy-piperidin-1-yl)-pentanoic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C 4: 2N aq. NaOH / methanol / Heating View Scheme

diphenylpyraline (147-20-6) → 6-(4-Benzhydryloxy-piperidin-1-yl)-hexanoic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C 4: 2N aq. NaOH / methanol / Heating View Scheme

diphenylpyraline (147-20-6) → ethyl 3-[4-(diphenylmethoxy)piperidin-1-yl]propanoate (133016-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C View Scheme

diphenylpyraline (147-20-6) → 5-(4-Benzhydryloxy-piperidin-1-yl)-pentanoic acid ethyl ester (661481-71-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C View Scheme

diphenylpyraline (147-20-6) → 6-(4-Benzhydryloxy-piperidin-1-yl)-hexanoic acid methyl ester (770685-45-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / toluene / 5.5 h / Heating 2: 88 percent / 40percent aq. NaOH / ethanol / 16.5 h / Heating 3: K2CO3 / dimethylformamide / 80 °C View Scheme

Upstream product

• 106-52-5 N-methyl-4-hydroxypiperidine 
• 91-01-0 1,1-Diphenylmethanol 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 908093-98-1 diazodiphenylmethane 
• 776-74-9 Bromodiphenylmethane 
• 90-99-3 diphenylchloromethane 

Downstream Products

• 65214-84-8 ethyl 4-(diphenylmethoxy)-1-piperidinecarboxylate 
• 770685-45-5 6-(4-Benzhydryloxy-piperidin-1-yl)-hexanoic acid methyl ester 
• 661481-71-6 5-(4-Benzhydryloxy-piperidin-1-yl)-pentanoic acid ethyl ester 
• 133016-99-6 ethyl 3-[4-(diphenylmethoxy)piperidin-1-yl]propanoate 
• 133015-42-6 ethyl <(4-diphenylmethoxy)piperidino>acetate 
• 133993-23-4 4-(4-Benzhydryloxy-piperidin-1-yl)-butyric acid 
• 58258-01-8 4-diphenylmethoxypiperidine 
• 125602-76-8 ethyl 4-(4-benzhydryloxypiperidino)butanoate 

Related news

Antimycobacterial activity of diphenylpyraline (cas 147-20-6) derivatives09/30/2019

2-Substituted derivatives of diphenylpyraline and their 1-phenyl and 1-phenethyl analogues have been prepared in several steps from dihydropyridine-2(1H)-thiones. The structures of all new compounds have been confirmed by NMR spectroscopy. Their activity against Mycobacterium tuberculosis H ...detailed

Effects of the histamine H1 receptor antagonist and benztropine analog diphenylpyraline (cas 147-20-6) on dopamine uptake, locomotion and reward09/29/2019

Diphenylpyraline hydrochloride (DPP) is an internationally available antihistamine that produces therapeutic antiallergic effects by binding to histamine H 1 receptors. The complete neuropharmacological and behavioral profile of DPP, however, remains uncharacterized. Here we describe stu...detailed

Relevant articles and documents

Synthesis and biological evaluation of new N-substituted 4-(arylmethoxy)piperidines as dopamine transporter inhibitors

The library of new N-substituted 4-(arylmethoxy)piperidines as dopamine transporter inhibitors was designed and synthesized. H-Bond donors in piperidine ring were found to be important for reduced locomotor activity in mice. 4-[Bis(4-fluorophenyl)methoxy]piperidine has IC50 17.0 ± 1.0 nm for dopamine transporter and locomotor activity, which is lower than that for cocaine.