CID 657365

Base Information

• Chemical Name: CID 657365
• CAS No.: 147-24-0
• Molecular Formula: C17H21NO^.HCl
• Molecular Weight: 291.821
• Hs Code.: 29221990
• Mol file: 147-24-0.mol

Synonyms:AKOS015914870

Chemical Property of CID 657365

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 168-172 °C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 343.7 °C at 760 mmHg
• Flash Point: 101.5 °C
• PSA: 12.47000
• Density: 1.024 g/cm³
• LogP: 4.15620
• Storage Temp.: Desiccate at RT
• Sensitive.: Light Sensitive
• Solubility.: Very soluble in water, freely soluble in alcohol.
• Water Solubility.: 1000 g/L
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 291.1389920
• Heavy Atom Count: 20
• Complexity: 211

Purity/Quality:

99%min ^*data from raw suppliers

Diphenhydramine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 36-45-36/37-16-7-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [H+].CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.[Cl-]
• Description: Diphenhydramine hydrochloride is an antihistamine drug having the chemical name 2-(Diphenylmethoxy)- N,N-dimethylethylamine hydrochloride. It occurs as a white, crystalline powder, is freely soluble in water and alcohol and has a molecular weight of 291.82. The molecular formula is C17H21NO·HCl and the structural formula is as follows: Diphenhydramine hydrochloride in the parenteral form is a sterile, pyrogen-free solution available in a concentration of 50 mg of diphenhydramine hydrochloride per mL. The solutions for parenteral use have been adjusted to a pH between 5.0 and 6.0 with either sodium hydroxide or hydrochloric acid and contains 0.1 mg/mL benzethonium chloride as a germicidal agent. Diphenhydramine is most commonly used as a first-generation antihistamine and is globally marketed in various brand formulations (Benadryl?, Unisom?, Tylenol?, Zzzquil?). It competitively blocks H1 receptors, thereby preventing the actions of histamine on bronchial smooth muscle, capillaries, and gastrointestinal (GI) smooth muscle. This prevents histamine-induced bronchoconstriction, vasodilation, increased capillary permeability, and GI smooth muscle spasms. Diphenhydramine exhibits anti-tussive, antiemetic, sedative, anti-allergic, and anticholinergic activities.
• Uses: Diphenhydramine is a H1-histamine receptor antagonist with anticholinergic (drying) and sedative side effects. It is categorized as an antihistaminic; sedative, hypnotic, treatment of allergic. It is used to treat allergy and cold symptoms such as sneezing, runny nose, watery eyes, urticaria (hives), skin rash, and pruritus (itchy skin).
• Therapeutic Function: Antihistaminic

Technology Process of CID 657365

There total 9 articles about CID 657365 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-diphenylmethoxy-N,N-dimethylethanamine (58-73-1) → diphenhydramine hydrochloride (147-24-0,8052-21-9)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 1h; Time;

Reference yield:

2-(N,N-dimethylamino)ethanol (108-01-0) + Bromodiphenylmethane (776-74-9) → diphenhydramine hydrochloride (147-24-0,8052-21-9)

Guidance literature:

2-(N,N-dimethylamino)ethanol; Bromodiphenylmethane; In toluene; for 20h; Reflux;

With hydrogenchloride; In diethyl ether; at 25 ℃;

DOI:10.1126/science.aav2211

Reference yield:

bromobenzene (108-86-1,52753-63-6) → diphenhydramine hydrochloride (147-24-0,8052-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium / 0.67 h / Reflux; Inert atmosphere

1.2: 5 h / Reflux; Inert atmosphere

2.1: toluene / 4 h / Reflux

3.1: toluene / 20 h / Reflux

3.2: 25 °C

With magnesium; In toluene; 3.1: |Williamson Ether Synthesis;

DOI:10.1126/science.aav2211

upstream raw materials:

benzhydryl-(2-hydroxy-ethyl)-dimethyl-ammonium; chloride

diphenylchloromethane

2-(N,N-dimethylamino)ethanol

2-diphenylmethoxy-N,N-dimethylethanamine

Downstream raw materials:

benzophenone

Diphenylmethane

Diphenhydramine-N-oxide

formic acid

Refernces

• 1、 Snead, David R.,Jamison, Timothy F.. "End-to-end continuous flow synthesis and purification of diphenhydramine hydrochloride featuring atom economy, in-line separation, and flow of molten ammonium salts". . p. 2822 - 2827. Retrieved 2013.
• 2、 -. "Method for preparing toluene benzyl phenyl substituted compound". Paragraph 0028; 0029; 0030; 0031. . Retrieved 2018/03/26.