2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL synthesis

Yield:24152-96-3 44%

Reaction Conditions:

with hydrogenchloride;palladium 10% on activated carbon in tetrahydrofuran;water; for 3 h;Inert atmosphere;

Steps:

Preparation of 4-(aminoacetyl)morpholine hydrochloride (19)

In a round-bottom 264 flask containing THF and 0.25 mL of 3.25 M HCl solution were added the azide 18, 265 followed by 10% palladium-on-charcoal. The suspension was saturated with H2 and 266 stirred under an H2 atmosphere for 3 hours. The reaction mixture was filtered through a 267 quantitative filter paper (pore size of 8 μm) and the filtrate was evaporated under reduced 268 pressure. The resulting oil was kept in desiccator for 24 h to yield the amine 19 as a yellow 269 solid, 44% yield, m.p. 131.4 - 132.8 C; IR (neat, cm-1) 3200 - 2400, 1652, 1104; 1H NMR (200 MHz, D2O) δ 3.98 (s, 2H), 3.78 - 3.67 (m, 4H), 3.58 (t, 2H, J = 4.5), 3.46 (t, 271 2H, J = 4.5); 13C NMR (DMSO-d6, 50 MHz) δ 165.7, 66.0, 65.8, 44.7, 42.2, 39.9.

References:

Braga, Saulo Fehelberg Pinto;Martins, Luan Carvalho;da Silva, Elany Barbosa;Sales Júnior, Policarpo Ademar;Murta, Silvane Maria Fonseca;Romanha, Alvaro José;Soh, Wai Tuck;Brandstetter, Hans;Ferreira, Rafaela Salgado;de Oliveira, Renata Barbosa [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 6,p. 1889 - 1900] Location in patent:supporting information