4-(2-Aminoethyl)tetrahydropyran

4-(2-Aminoethyl)tetrahydropyran - Names and Identifiers

Name	4-(2-Aminoethyl)tetrahydropyran
Synonyms	4-(AMinoethyl)tetrahydrop... 4-Aminoethyl-tetrahydropyrane 4-(2-AMINOETHYL)TETRAHYDROPYRAN 4-(2-Aminoethyl)tetrahydropyran 4-(2-Aminoethyl)tetrahydropyrane 4-(2-Aminoethyl)tetrahydro-2H-pyran 2-(TETRAHYDRO-PYRAN-4-YL)-ETHYLAMINE 2-(tetrahydro-2H-pyran-4-yl)ethanamine 2-(tetrahydro-2H-pyran-4-yl)ethanaminium
CAS	65412-03-5
EINECS	145-589-6
InChI	InChI=1/C7H15NO/c8-4-1-7-2-5-9-6-3-7/h7H,1-6,8H2/p+1

4-(2-Aminoethyl)tetrahydropyran - Physico-chemical Properties

Molecular Formula	C7H15NO
Molar Mass	129.2
Density	0.931±0.06 g/cm3(Predicted)
Boling Point	88-89°C 13mm
Flash Point	74.2°C
Solubility	Chloroform (Slightly), Methanol (Slightly)
Vapor Presure	0.324mmHg at 25°C
Appearance	Oil
Color	Clear Colourless
pKa	10.34±0.10(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,2-8°C

4-(2-Aminoethyl)tetrahydropyran - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R36/37/38 - Irritating to eyes, respiratory system and skin. R41 - Risk of serious damage to eyes R37/38 - Irritating to respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S39 - Wear eye / face protection. S36 - Wear suitable protective clothing.
HS Code	29339900
Hazard Note	Irritant/Keep Cold

4-(2-Aminoethyl)tetrahydropyran - Reference Information

overview

4-(2-aminoethyl) tetrahydropyran is one of the main raw materials of the new drug befopram, which directly affects the cost, scale and subsequent promotion and application of befopram. In the prior art, with regard to the synthesis of 4-(2-aminoethyl) tetrahydropyran, method 1 is the reaction of pyrone and diethyl cyanomethyl phosphate to generate 4-(2-aminoethyl) tetrahydropyran; method 2 is the reaction of tetrahydro-2H-pyran-4-propionic acid with sodium azide to generate 4-(2-aminoethyl) tetrahydropyran; method 3 is the reaction of 4-chlorotetrahydropyran with methyl cyanoacetate to produce 4-(2-aminoethyl) tetrahydropyran.

preparation method

the molar ratio of 4-chlorotetrahydropyran to methyl cyanoacetate is 0.9:1; The hydrogen pressure is 1MPa.
1)4-chlorotetrahydropyran A80.4g(0.67mol), methyl cyanoacetate 73g(0.74mol), potassium tert-butoxide 75g(0.67mol) are dissolved in 100ml of toluene, stirred at 50 ℃ for 12h, heated to 110 ℃ for 12h, the reaction is completed, the reaction liquid is washed with 300ml of water for 3 times, and the organic phase is concentrated under reduced pressure, 113.6g(0.62mol) of 2-cyano -2-(tetrahydro-4-pyranyl) methyl acetate was obtained.
2) 113.6g(0.62mol) of 2-cyano -2-(tetrahydro-4-pyranyl) methyl acetate, 10.8ml of water, 10.8g of sodium chloride and 540ml of dimethyl sulfoxide are added to the flask, stirred at 150 ℃ for 8h, distilled, and 1000ml of water is added for stirring, the organic phase was extracted 4 times with 1000ml of diethyl ether, washed with water and saturated salt water respectively, the organic phase was dried and decolorized, and 75g(0.60mol) of oil (tetrahydro-4-pyranyl)-acetonitrile was obtained by distillation.
3)(tetrahydro-4-pyranyl) -75g(0.60mol), Pd/C2.5g and 400ml of ethanol were added to the hydrogenation kettle, replace for 3 times, hydrogenate, maintain pressure of 1MPa, temperature of 25 ℃, stir reaction for 12 hours, filter the reaction liquid after reaction, transfer the filtrate to a flask, and distill under reduced pressure to obtain 65.8g(0.51mol) of 4-(2-aminoethyl) tetrahydropyran oil. The yield of 4-(2-aminoethyl) tetrahydropyran was 76.1% and the purity was 98.5%.

Last Update：2024-04-09 19:05:04