ChemicalBook CAS DataBase List 3-Amino-6-morpholinopyridine

3-Amino-6-morpholinopyridine synthesis

8synthesis methods

Product Name:3-Amino-6-morpholinopyridine
CAS Number:52023-68-4
Molecular formula:C9H13N3O
Molecular Weight:179.22

110-91-8 Synthesis

110-91-8
687 suppliers
$9.00/1g

4548-45-2 Synthesis

4548-45-2
540 suppliers
$6.00/5g

52023-68-4
126 suppliers
$45.00/50mg

Yield:52023-68-4 93%

Reaction Conditions:

Stage #1:morpholine;2-chloro-5-nitropyridine with triethylamine in dichloromethane at 20; for 12 h;
Stage #2: with palladium on activated charcoal;hydrogen in ethanol under 1125.11 Torr; for 2 h;

Steps:

3.1.3. Synthesis of 6-Morpholinopyridin-3-amine (6)
A mixture of 2-chloro-5-nitropyridine (303 mg, 1.91 mmol, 1.0 equiv), morpholine (0.5 mL,5.74 mmol, 3.0 equiv) and Et3N (483 mg, 0.67 mL, 2.5 equiv) in CH2Cl2 (4 mL) was stirred at roomtemperature overnight. The reaction mixture was diluted with water (10 mL) and extracted withCH2Cl2 (30 mL 3). The combined organic layers were washed with water (30 mL 6) and brine(1x30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give a yellow solid. 70 mg ofthe yellow solid (0.335 mmol, 1.0 eq) were diluted in EtOH (5 mL) and a spatula tip of catalyst Pd/Cwas added. The obtained mixture was hydrogenated for 2 h, using a Hypem XP hydrogen generator(h2planet, Milan, Italy), Pressure was set at 1.5 bar. The crude mixture was filtered on Celite, and thefiltrate was evaporated to obtain a red solid. Yield: 93% over two steps. TLC (hexane:ethyl acetate =4:6 v/v + Et3N): Rf = 0.15. 1H-NMR (CDCl3) δ 7.79 (d, J = 2.7 Hz, 1H), 7.01 (dd, J = 8.8, 2.7 Hz, 1H),6.73 (brs, 2H, NH2), 6.56 (d, J = 8.8 Hz, 1H), 3.82 (m, 4H), 3.33 (m, 4H). 13C-NMR (CDCl3) δ 154.02,135.09, 134.58, 126.42, 108.41, 66.80 (2C), 47.08 (2C). ESI()MS: m/z 178 [M-H]-.

References:

Bosco, Bartolomeo;Defant, Andrea;Messina, Andrea;Incitti, Tania;Sighel, Denise;Bozza, Angela;Ciribilli, Yari;Inga, Alberto;Casarosa, Simona;Mancini, Ines [Molecules,2018,vol. 23,# 8,art. no. 1996]

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