Doxylamine

Base Information

• Chemical Name: Doxylamine
• CAS No.: 469-21-6
• Molecular Formula: C17H22 N2 O
• Molecular Weight: 270.374
• European Community (EC) Number: 207-414-2
• UNII: 95QB77JKPL
• DSSTox Substance ID: DTXSID1022970
• Nikkaji Number: J5.925K
• Wikipedia: Doxylamine
• Wikidata: Q423390
• NCI Thesaurus Code: C61738
• RXCUI: 3642
• Pharos Ligand ID: DXTRAP97HAY5
• Metabolomics Workbench ID: 37942
• ChEMBL ID: CHEMBL1004
• Mol file: 469-21-6.mol

Synonyms:Doxylamine

Chemical Property of Doxylamine

Chemical Property:

• Melting Point: 25°C
• Refractive Index: 1.5486 (estimate)
• Boiling Point: 364.9 °C at 760 mmHg
• PKA: pKa 9.20(H2O t = 25 c = 0.002–0.01) (Uncertain);4.4 (Uncertain);9.2 (Uncertain)
• Flash Point: 174.5 °C
• PSA: 25.36000
• Density: 1.043 g/cm³
• LogP: 2.92330
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 270.173213330
• Heavy Atom Count: 20
• Complexity: 276

Purity/Quality:

99.9% ^*data from raw suppliers

(±)-Doxylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C
• Recent ClinicalTrials: Pharmacokinetics and Bioequivalence of Doxylamine + Pyridoxine, Film-coated, Enteric-soluble Tablets, and Diclectin, Delayed Release Tablets, in Healthy Volunteers
• Uses: Antihistaminic. (±)-Doxylamine is an intermediate in the synthesis of Doxylamine N, N’-Dioxide (D562025), which is an impurity of Doxylamine (succinate salt, D562000), which is an H1 Histamine receptor antagonist.

Technology Process of Doxylamine

There total 6 articles about Doxylamine 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: 98.0%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + 1-phenyl-1-(pyridin-2-yl)ethanol (19490-92-7) → doxylamine (469-21-6)

Guidance literature:

1-phenyl-1-(pyridin-2-yl)ethanol; With sodium amide; In 5,5-dimethyl-1,3-cyclohexadiene; Inert atmosphere;

(2-chloroethyl)dimethylamine hydrochloride; In 5,5-dimethyl-1,3-cyclohexadiene; for 1h; Time; Reflux;

Reference yield: 91.0%

2-(dimethylamino)ethyl chloride (107-99-3) + 1-phenyl-1-(pyridin-2-yl)ethanol (19490-92-7) → doxylamine (469-21-6)

Guidance literature:

With tetrabutylammomium bromide; potassium; In toluene; at 110 ℃; for 1.6h; Reagent/catalyst; Temperature; Solvent;

Reference yield:

2-(dimethylamino)ethyl chloride (107-99-3) → doxylamine (469-21-6)

Guidance literature:

With toluene;

DOI:10.1021/ja01192a010

upstream raw materials:

2-(dimethylamino)ethyl chloride

(2-chloroethyl)dimethylamine hydrochloride

1-phenyl-1-(pyridin-2-yl)ethanol

iodobenzene

Downstream raw materials:

2-(1-phenylvinyl)pyridine

1-phenyl-1-(pyridin-2-yl)ethanol

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-dimethyl-[2-(1-phenyl-1-pyridin-2-yl-ethoxy)-ethyl]-ammonium; chloride

doxylamine succinate

Refernces

• 1、 -. "Synthesis method of doxylamine succinate". Paragraph 0056-0057; 0059-0060; 0062-0063; 0065-0068. . Retrieved 2019/12/09.
• 2、 -. "A method for preparing many west pulls sensitively succinic acid". . . Retrieved 2017/03/08.