ChemicalBook CAS DataBase List 2,5,8,11,14,17-Hexaoxanonadecan-19-amine

2,5,8,11,14,17-Hexaoxanonadecan-19-amine synthesis

7synthesis methods

Product Name:2,5,8,11,14,17-Hexaoxanonadecan-19-amine
CAS Number:184357-46-8
Molecular formula:C13H29NO6
Molecular Weight:295.37

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2,5,8,11,14,17-Hexaoxanonadecan-19-amine

184357-46-8
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Yield: 98%

Reaction Conditions:

Stage #1:1-azido-2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethane with triphenylphosphine in tetrahydrofuran at 20; for 5 h;
Stage #2: with water in tetrahydrofuran at 80;

Steps:

2.4 Example 2
Methoxy hexa-(ethyleneglycol)-(amine) (7; HexaGME-NH₂): Triphenylphosphine (10.88 g, 41.5 mmol, 1.25 eq.) in 25 mL of anhydrous THF was added dropwise to a solution of methoxy-hexa-(ethylene glycol)-azide 6 (10.6 g, 33 mmol, 1 eq.) in anhydrous THF (25 mL), and the solution was stirred at RT for 5 hours.
Distilled water (20 mL) was then added and the mixture was heated under reflux (80°C) and vigorously stirred overnight.
The resulting mixture was evaporated under reduced pressure and the residue was purified by flash chromatography using CH₂Cl₂:MeOH 9:1 (+ 1% Et₃N) as eluent to afford 9.55 g of 7 (98 %) as a pale yellow oil. ¹H-NMR (250 MHz, CDCl₃) δ (ppm): 1.78 (s, 2H, -CH₂-NH₂), 2.76 (t, 2H, ³J_H-H = 5.25 Hz, -CH₂-CH₂-NH₂), 3.26 (s, 3H, -O-CH₃), 3.39-3.46 (m, 4H, -O-CH₂-CH₂-O- + -O-CH₂-CH₂-NH₂), 3.51-3.56 (m, 18H, 4 * -O-CH₂-CH₂-O- + -O-CH₂-CH₂-O-); ¹³C-NMR (62.9 MHz, CDCl₃) δ (ppm): 72.8, 71.6, 70.3, 70.3, 70.3, 70.2, 70.2, 70.2, 70.0, 58.7, 41.4; ESI-MS (ion trap): m/z 296 [M+H]⁺.

References:

Mattarei, Andrea;Biasutto, Lucia;Zoratti, Mario;Paradisi, Cristina;Marotta, Ester;Garbisa, Spiridione;Azzolini, Michele;Bradaschia, Alice;Carraro, Massimo;Sassi, Nicola EP2774915, 2014, A1 Location in patent:Paragraph 0058; 0061

23601-40-3 Synthesis