469-21-6

Basic information

• Product Name: DOXYLAMINE
• Synonyms: N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine;NCI C60684;Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether;Pyridine, 2-[alpha-[2-(dimethylamino)ethoxy]-alpha-methylbenzyl]-;DOXYLAMINE;dimethyl(2-(1-phenyl-1-(2-pyridyl)ethoxy)ethyl)amine;2-[a-(2-dimethylaminoethoxy)-a-methylbenzyl]pyridine;2-dimethylaminoethoxyphenylmethyl-2-picoline
• CAS NO: 469-21-6
• Molecular Formula: C₁₇H₂₂N₂O
• Molecular Weight: 270.37
• EINECS: 207-414-2
• Mol File: 469-21-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 25°C
• Boiling Point: bp0.5 137-141°
• Flash Point: 174.5 °C
• Appearance: /
• Density: 1.0023 (rough estimate)
• Refractive Index: 1.5486 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: pKa 9.20(H2O t = 25 c = 0.002–0.01) (Uncertain);4.4 (Uncertain);9.2 (Uncertain)
• Stability: Temperature Sensitive
• CAS DataBase Reference: DOXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DOXYLAMINE(469-21-6)
• EPA Substance Registry System: DOXYLAMINE(469-21-6)

Safety Data

• Hazardous Substances Data: 469-21-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 469-21-6 differently. You can refer to the following data:
1. Antihistaminic.
2. (±)-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.

Brand name

Decapryn (Sanofi Aventis); Unisom (Pfizer).

General Description

Clear colorless liquid.

Reactivity Profile

DOXYLAMINE is an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides

InChI:InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3

Upstream product

• 107-99-3 2-(dimethylamino)ethyl chloride 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 19490-92-7 1-phenyl-1-(pyridin-2-yl)ethanol 
• 591-50-4 iodobenzene 
• 1122-62-9 2-acetylpyridine 
• 14159-54-7 2-(1-phenylethyl)pyridine 

Downstream Products

• 15260-65-8 2-(1-phenylvinyl)pyridine 
• 19490-92-7 1-phenyl-1-(pyridin-2-yl)ethanol 
• 145823-16-1 ((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 
• 562-10-7 doxylamine succinate 

Relevant articles and documents

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

Preparation method of doxylamine succinate

The invention discloses a preparation method of doxylamine succinate. The preparation method comprises following steps: step 1, 2-pyridyl phenyl methyl carbinol is dissolved in an organic solvent, and is reacted with 2-dimethylaminoethyl chloride hydrochloride at high temperature, after reaction, target product N,N-dimethyl-2-[1-phenyl-1-(2-pyridine)oxethyl]ethylamine is obtained via quenching extracting separation; and step 2, N,N-dimethyl-2-[1-phenyl-1-(2-pyridine) oxethyl]ethylamine obtained in the step 1 and succinic acid are subjected to salt forming in an organic solvent; and finished product N,N-dimethyl-2-(1-phenyl-1-(2-pyridine)ethoxy)ethanamine succinate (doxylamine succinate) is obtained via cooling crystallization. The preparation method is simple, safe, and reliable, is high in doxylamine succinate yield, and is suitable for industrialized enlarged production; and post-treatment is simple and convenient.