147-20-6

Usage

Uses

Used in Allergy Treatment:
Diphenylpyraline is used as a sedating antihistamine, particularly for the symptomatic relief of allergic conditions such as rhinitis and hay fever. It helps alleviate symptoms like sneezing, itching, and watery eyes by blocking the action of histamine, a substance released during an allergic reaction.
Used in Skin Disorder Treatment:
Diphenylpyraline is also utilized in the treatment of pruritic skin disorders, where it provides relief from itching and irritation. Its antihistamine properties help reduce inflammation and discomfort associated with various skin conditions.
Used in Cough and Cold Remedies:
Furthermore, diphenylpyraline is used as the teoclate salt (piprinhydrinate) in compound preparations for the symptomatic relief of coughs and the common cold. It helps suppress the cough reflex and provides temporary relief from the discomfort associated with coughing and cold symptoms.

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 
• 90-99-3 diphenylchloromethane 
• 776-74-9 Bromodiphenylmethane 
• 908093-98-1 diazodiphenylmethane 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

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

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Relevant academic research and scientific papers

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.

Sigma receptor ligands and the use thereof

PCT No. PCT/US94/07121 Sec. 371 Date Feb. 21, 1996 Sec. 102(e) Date Feb. 21, 1996 PCT Filed Jun. 23, 1994 PCT Pub. No. WO95/00131 PCT Pub. Date Jan. 5, 1995The invention relates to methods for the treatment of central nervous system disorders, neurological disorders, gastrointestinal disorders, drug abuse, angina, migraine, hypertension and depression by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.