ChemicalBook CAS DataBase List methyl 3-(methylamino)propanoate

methyl 3-(methylamino)propanoate synthesis

6synthesis methods

Product Name:methyl 3-(methylamino)propanoate
CAS Number:24549-12-0
Molecular formula:C5H11NO2
Molecular Weight:117.15

64-17-5 Synthesis

64-17-5
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17946-01-9
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24549-12-0
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$40.00/250mg

2213-08-3 Synthesis

2213-08-3
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Yield:-

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon at 20; for 48 h;Inert atmosphere;

Steps:

3
A Schlenk tube was charged with methyl 3-(benzyl (methyl) amino) propanoate (2 g, 9.64 mmol) and dissolved in EtOH (60 mL) . To this solution were added 500 mg of 10% Pd/C in small portions . The atmosphere of the tube was purged first with oxygen-free N₂ followed by H₂. A double-layer latex balloon filled with H₂ ( ~ 1 L) was then attached to the Schlenk tube and the reaction was left stirring at room temperature for 48 h, during which the balloon was refilled as needed with H₂. At this point, the flask was opened and Celite added to the reaction mixture followed by filtration with Celite . The filtrate was evaporated to dryness to yield a yellowish oil. ¹H- and ¹³C-NMR confirmed complete amine deprotection. However, it was also noted that transesterification had occurred to some extent:The crude product was used for the next step without modification. Thus, the mixture of methyl and ethyl esters was dissolved in 40 mL of 5 M HCl and refluxed for 16 h. The solvent was then evaporated under vacuum to yield the product as a hygroscopic white solid (0.969 g, 72 %) . ¹H-NMR (D₂O, 400.3 MHz, 298 K) δ_H (ppm) 3.33 (t, J = 6.4 Hz, 2H, -N-CIi₂-CH₂-), 2.85 (t, J = 6.4 Hz, 2H, -CH₂-COOH) , 2.76 (s, 3H, -N-CH₃) ; ¹³C-NMR (D₂O, 100.7 MHZ, 298 K) S_c (ppm) 174.32 (- COOH) , 44.56 (-NH-CH₂-) , 33.08 (- CH₂-CH₂-), 30.05 (-NH-CH₃) . Found: C, 34.37; H, 7.35; N, 9.88. C₄H₁₀ClNO₂ requires: C, 34.42; H, 7.22; N, 10.03.