2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride

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CAS:35604-67-2
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2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride Basic information
Product Name:2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride
Synonyms:Morpholine, 2-(2-ethoxyphenoxy)methyl-, hydrochloride;ICI-58834;Vivalan;rac Viloxazine Hydrochloride;2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride;(+/-)-2-(o-EthoxyphenoxyMethyl)Morpholine;Catatrol;Vicilan
CAS:35604-67-2
MF:C13H20ClNO3
MW:273.7558
EINECS:252-638-6
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:35604-67-2.mol
2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride Structure
2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride Chemical Properties
Melting point 178-180°C
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
color White to Off-White
Safety Information
HazardClass IRRITANT
ToxicityLD50 in mice (mg/kg): 1000 orally, 60 i.v. (Brosnan)
MSDS Information
2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride Usage And Synthesis
Chemical PropertiesOff-White Solid
OriginatorVivalan,I.C.I. ,UK,1974
UsesRac Viloxazine Hydrochloride is research useful chemical used as an antidepressant.
Manufacturing Process2-Ethoxyphenol is first reacted with epichlorohydrin to give 1,2-epoxy-3-(o- ethoxyphenoxy)-propane.
A mixture of crude (83%) 1,2-epoxy-3-(o-ethoxyphenoxy)propane (19.4 grams), 70.5 grams 2-aminoethyl hydrogen sulfate, 40.0 grams sodium hydroxide, 400 ml ethanol and 200 ml water is stirred at 60°C for 18 hours and is then evaporated to dryness. The residue is dissolved in 200 ml water and the mixture is extracted three times with 150 ml of diethyl ether each time. The combined extracts are dried over magnesium sulfate and evaporated to dryness, The crude product (21.5 grams) is dissolved in isopropanol (20 ml), 10.5 ml concentrated aqueous hydrochloric acid and 75 ml ethyl acetate are added and the mixture is cooled. The mixture is filtered and there is thus obtained as solid product 2-(o-ethoxyphenoxymethyl) morpholine hydrochloride, MP 179° to 182°C (8.6 grams; 38% yield based on total epoxide used), according to US Patent 3,712,890.
Therapeutic FunctionPsychotropic
2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride Preparation Products And Raw materials
Raw materials2-Ethoxyphenol-->Epichlorohydrin-->2-AMINOETHYL HYDROGEN SULFATE-->2-Propanol, 1-(2-ethoxyphenoxy)-3-[(2-hydroxyethyl)(phenylmethyl)amino]--->2-[(2-ethoxyphenoxy)methyl]oxirane
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