Synthesis of 1-Alkylamino-4-bromopentane Derivatives and of Other Amino Halides¹

Influence of solvent on the motion of molecules immobilized on polystyrene matrices and on glass surfaces

“…Evidence in support of this theory was obtained by treating 5a in dry pyridine with bis(trimethylsi1yl)trifluoroacetamide yielding 5b. 20 The room-temperature EPR spectra of 5a and 5b in the dry state were similar. By using either hydrogen-or nonhydrogen-bonding solvents to wet the surface of 5b, the estimated rotational correlation times varied only from 0.8 X to 3.6 X sec.…”

Vesicular Properties of Stereoisomeric Surfactants

“…(4 R ,5 R )-4,5-Bis((hexadecyloxy)methyl)-2-methyl-2-(3-acetoxypropyl)-1,3-dioxolane [(4 R ,5 R )-7]. A mixture of 2.30 g (4.03 mmol) of (+)- 6 , 1.15 g (7.98 mmol) of 5-acetoxy-2-pentanone, 0.13 g (0.52 mmol) of pyridinium p -toluenesulfonate (PPTS), and 100 mL of C 6 H 5 Me was refluxed for 4 days under a Dean-Stark trap fitted with a drying tube (CaCl 2 ). After 0.75 g (7.08 mmol) of Na 2 CO 3 was added, the reaction mixture was filtered and chromatographed on a 2- × 20-cm column of neutral aluminum oxide (J. T. Baker 0537) packed in hexane and eluted with 3:7 Et 2 O−hexane to give 2.10 g (75%) of the title compound as an oil: 1 H NMR (270 MHz) δ 4.00−4.10 (m, 3 H, CH 3 CO 2 C H 2 CH 2 CH 2 , CHO), 3.83−3.90 (m, 1 H, CHO), 3.55 (t, J = 5.0, 4 H, 2 CH 2 C H 2 OCH 2 ), 3.41−3.51 (m, 4 H, 2 CH 2 CH 2 OC H 2 ), 2.03 (s, 3 H, C H 3 CO 2 CH 2 CH 2 CH 2 ), 1.75 (m, 4 H, CH 3 CO 2 CH 2 C H 2 C H 2 ), 1.58 (m, 4 H, 2 C H 2 CH 2 OCH 2 ), 1.38 (s, 3 H, CH 3 CO 2 ), 1.25 (s, 52 H, 2 (CH 2 ) 13 ), 0.88 (t, 6 H, 2 CH 3 ); 13 C NMR (270 MHz) δ 170.98, 110.55, 78.04, 77.27, 71.83, 71.47, 71.09, 64.48, 36.12, 31.86, 29.63, 29.56, 29.49, 29.42, 29.29, 26.02, 25.54, 22.84, 22.61, 29.86, 14.04.…”

An Update on Pharmacological Relevance and Chemical Synthesis of Natural Products and Derivatives with Anti SARS‐CoV‐2 Activity

“…Further, the reaction of 55 with 4‐diethylamino‐1‐methylbutylamine ( 59 ) under Suzuki coupling condition afforded the desired final product quinolone in 74 % yield. In addition, a considerable number of methods are reported for the synthesis of 59 as well [120–121] . The treatment of 3‐acetylbutyrolactone ( 56 ) prepared from acetoacetic acid ester and ethylene oxide) with acid, HBr leads to ester hydrolysis followed by decarboxylation to produce 1‐bromo‐4‐pentanone ( 57 ).…”

“…In addition, a considerable number of methods are reported for the synthesis of 59 as well. [120][121] The treatment of 3-acetylbutyrolactone (56) prepared from acetoacetic acid ester and ethylene oxide) with acid, HBr leads to ester hydrolysis followed by decarboxylation to produce 1-bromo-4-pentanone (57). The reaction of 57 with diethylamine resulted in a substitution reaction to afford 1diethylamino-4-pentanone (58), which was then subjected to reductive amination using H 2 , NH 3 , and Raney nickel as a catalyst to produce the desired compound 4-diethyl-1-methylbutylamine (59) in decent yield.…”