Toladryl

Base Information

• Chemical Name: Toladryl
• CAS No.: 19804-27-4
• Molecular Formula: C18H23 N O
• Molecular Weight: 269.387
• Hs Code.: 2922199695
• European Community (EC) Number: 243-329-7
• UNII: P9633413CU
• DSSTox Substance ID: DTXSID20903322
• Nikkaji Number: J690.823C,J8.577D
• Wikipedia: 4-Methyldiphenhydramine
• Wikidata: Q4637175
• Mol file: 19804-27-4.mol

Synonyms:Toladryl;19804-27-4;4-Methyldiphenhydramine;p-Methyldiphenhydramine;N,N-dimethyl-2-[(4-methylphenyl)-phenylmethoxy]ethanamine;UNII-P9633413CU;Ethanamine, N,N-dimethyl-2-[(4-methylphenyl)phenylmethoxy]-;EINECS 243-329-7;P9633413CU;N,N-Dimethyl-2-[(4-methylphenyl)phenylmethoxy]ethanamine;2-((p-Methyl-alpha-phenylbenzyl)oxy)ethyl(dimethyl)amine;Diphenhydramine Impurity B;(R)-Neobenodine;Ethanamine, N,N-dimethyl-2-((4-methylphenyl)phenylmethoxy)-;2-[(p-methyl-alpha-phenylbenzyl)oxy]ethyl(dimethyl)amine;Ethylamine, N,N-dimethyl-2-[(p-methyl-.alpha.-phenylbenzyl)oxy]-;ETHYLAMINE, N,N-DIMETHYL-2-((P-METHYL-.ALPHA.-PHENYLBENZYL)OXY)-;p-Methylbenzhydryl 2-Dimethylaminoethyl Ether;SCHEMBL28837;ORPHENADRINE IMPURITY F;P-METHYL DIPHENHYDRAMINE;DIMENHYDRINATE IMPURITY G;DTXSID20903322;P-METHYLDIPHENHYDRAMINE [MI];(+/-)-4-METHYLDIPHENHYDRAMINE;P-METHYL DIPHENHYDRAMINE [WHO-DD];FT-0675266;4-METHYLDIPHEN HYDRAMINE [USP IMPURITY];DIMENHYDRINATE IMPURITY G [EP IMPURITY];Q4637175;ORPHENADRINE CITRATE IMPURITY F [EP IMPURITY];N,N-dimethyl-2-[(p-methyl-alpha-phenylbenzyl)oxy]ethylamine;DIPHENHYDRAMINE HYDROCHLORIDE IMPURITY B [EP IMPURITY];Ethanamine, 2-[(4-methylphenyl)(phenyl)methoxy]-N,N-dimethyl-;P-METHYLBENZHYDRYL 2-DIMETHYLAMINOETHYL ETHER [WHO-DD];N,N-DIMETHYL-N-(2-(P-METHYL-.ALPHA.-PHENYLBENZYLOXY)ETHYL)AMINE

Chemical Property of Toladryl

Chemical Property:

• Melting Point: 151-155 °C
• Boiling Point: 362.5°Cat760mmHg
• PKA: 8.73±0.28(Predicted)
• Flash Point: 107°C
• PSA: 12.47000
• Density: 1.014g/cm³
• LogP: 3.66260
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 269.177964357
• Heavy Atom Count: 20
• Complexity: 252

Purity/Quality:

99%, ^*data from raw suppliers

Toladryl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C2=CC=CC=C2)OCCN(C)C
• Uses: A diphenylhydramine analog classified as an antihistaminic. A diphenhydramine (D486900) analog classified as an antihistaminic.

Technology Process of Toladryl

There total 23 articles about Toladryl 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: 94.0%

dimethyl amine (124-40-3) + 1-[(2-iodoethoxy)(phenyl)methyl]-4-methylbenzene → dimethyl-[2-(phenyl-p-tolyl-methoxy)-ethyl]-amine (19804-27-4)

Guidance literature:

In ethanol; water; at 20 ℃; for 72h;

DOI:10.1002/1099-0690(200111)2001:21<4137::AID-EJOC4137>3.0.CO;2-4

Reference yield: 81.0%

N,N-dimethyl-2-((S)-(4-methylphenyl)(phenyl)methoxy)acetamide → (S)-neobenodine (15832-68-5,19804-27-4,33431-07-1,33431-08-2)

Guidance literature:

With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 ℃; for 4h; optical yield given as %ee; enantioselective reaction; Reflux;

DOI:10.1002/chem.201200379

Reference yield: 58.0%

4-methylphenyl(phenyl)methanol (1517-63-1) + 2-(dimethylamino)ethyl chloride (107-99-3) → dimethyl-[2-(phenyl-p-tolyl-methoxy)-ethyl]-amine (19804-27-4)

Guidance literature:

With sodium hydride; In toluene; for 5h; Heating;

DOI:10.1002/ardp.19963290206

upstream raw materials:

2-(N,N-dimethylamino)ethanol

p-methyl-a-phenylbenzylchloride

4-methylphenyl(phenyl)methanol

2-(dimethylamino)ethyl chloride

Downstream raw materials:

C₁₈H₂₃NO₂

7-{Methyl-[2-(phenyl-p-tolyl-methoxy)-ethyl]-amino}-heptanenitrile

N¹-Methyl-N¹-[2-(phenyl-p-tolyl-methoxy)-ethyl]-heptane-1,7-diamine

(+/-)-(2-methylaminoethyl)-1-(3-methylphenyl)-1-phenylmethyl ether

Refernces

• 1、 Sui, Yao-Zong,Zhang, Xi-Chang,Wu, Jun-Wen,Li, Shijun,Zhou, Ji-Ning,Li, Min,Fang, Wenjun,Chan, Albert S. C.,Wu, Jing. "CuII-catalyzed asymmetric hydrosilylation of diaryl- and aryl heteroaryl ketones: Application in the enantioselective synthesis of orphenadrine and neobenodine". supporting information; experimental part. p. 7486 - 7492. Retrieved 2012/07/27.
• 2、 Wolf, Cornelia,Schunack, Walter. "Synthesis and pharmacology of combined histamine H1-/H2-receptor antagonists containing diphenhydramine and cyproheptadine derivatives". . p. 87 - 94. Retrieved 2007/10/02.