ChemicalBook CAS DataBase List N-METHYLPROPARGYLAMINE

N-METHYLPROPARGYLAMINE synthesis

6synthesis methods

Product Name:N-METHYLPROPARGYLAMINE
CAS Number:35161-71-8
Molecular formula:C4H7N
Molecular Weight:69.11

106-96-7 Synthesis

106-96-7
332 suppliers
$30.00/25g

74-89-5 Synthesis

74-89-5
7 suppliers
$13.44/25ML

35161-71-8
95 suppliers
$17.67/250mgs:

Yield:35161-71-8 55%

Reaction Conditions:

in water at 20;

Steps:

Allyl(methyl)amine (1a) and methyl(prop-2-ynyl)amine (1b) (general procedure).
General procedure: Allyl chloride or propargyl bromide in a 4 : 1 molar ratio, respectively, was added in portions from a dropping funnel to a 40% aqueous solution of methylamine at room temperature under constant stirring. The solution was stirred at room temperature for 3-4 h and then carefully acidified with HCl. The mixture was then treated with ether to extract unreacted halide. The amine hydrochloride solution was concentrated under reduced pressure and then transferred to a Favorsky flask equipped with aLiebig condenser and a receiver cooled by ice. A highly concentrated KOH solution was slowly added through a dropping funnel to a heated reaction mixture. The fractions boiling at 40-70°C (1a) and 45-92°C (1b) were collected, dried over MgSO₄, and placed into a refrigerator. A day after, the amine layer was decanted, dried over MgSO₄, and distilled from a Favorsky flask. Allyl(methyl)amine (1a). Yield 6 g (65%), bp 64-66°C (760 mmHg), n^D₂₀ 1.4110, mp (picrate) 106-108°C; the physicochemical constants are consistent with published data [1, 4]. ¹H NMR spectrum (300.077 MHz,DMSO-d6 + CCl4), δ, ppm: 1.28 br.s (1H, NH), 2.32 s(3H, CH3), 3.11 dt (2H, CH2, J 5.8, 1.5 Hz), 5.01 d.d.t(1H, =CH2, J 10.2, 2.0, 1.5 Hz), 5.11 d.d.t (1H, =CH2,J 17.2, 2.0, 1.5 Hz), 5.81 d.d.t (1H, =CH, J 17.2, 10.2,5.8 Hz). ¹³C NMR spectrum (75.465 MHz, DMSO-d6 +CCl4), δ, ppm: 35.2 (CH3), 53.7 (CH2), 114.6 (=CH2),136.8 (=CH). Found, %: C 67.34; H 12.61; N 19.52.C4H9N. Calculated, %: C 67.55; H 12.75; N 19.69.

References:

Ayrapetyan, L. V.;Chukhajian, E. O.;Mkrtchyan, H. S.;Panosyan, H. A. [Russian Journal of Organic Chemistry,2020,vol. 56,# 2,p. 353 - 355][Zh. Org. Khim.,2020,vol. 56,# 2,p. 319 - 322,4]

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106-95-6 Synthesis