ChemicalBook CAS DataBase List N,N-Diethylpropargylamine

N,N-Diethylpropargylamine synthesis

11synthesis methods

Product Name:N,N-Diethylpropargylamine
CAS Number:4079-68-9
Molecular formula:C7H13N
Molecular Weight:111.18

According to the processing condition difference reported at present, two kinds of synthesis techniques, respectively atmospheric low-temperature alkalization method and high-pressure catalysis method. The atmospheric low-temperature alkalization method generally is divided into two steps: 1) propionic alcohol reacts with phosphorus trichloride and generates propine chlorine under cold conditions; 2) upper step gained propine chlorine is reacted with diethylamine under the low-temperature alkali condition and generate N, N-diethyl propargylamine. As shown in the reaction formula:
N,N-Diethylpropargylamine

109-89-7
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106-96-7 Synthesis

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4079-68-9
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Yield: 94%

Reaction Conditions:

with potassium carbonate in toluene at 20; for 15 h;

Steps:

16.1 Step 1:
Step 1:
Synthesis of N,N-diethylprop-2-yn-1-amine
To a solution of diethylamine (0.46 ml, 1 eq) in toluene (10 ml) was added with K₂CO₃(1.23 g, 2 eq) and 3-bromoprop-1-yne (0.56 ml, 1.5 eq).
The mixture was stirred for 15 hr at room temperature and filtered off, and the filtrate was concentrated in vacuo.
The resulting residue was purified with column chromatography to prepare the title compound (0.46 g, 94%).
MS (ESI, m/z): 112.1 [M+H]⁺.

References:

Dong-A St Co., Ltd.;Choi, Sun-Ho;Im, Weon-Bin;Choi, Sung-Hak;Cho, Chong-Hwan;Moon, Ho-Sang;Park, Jung-Sang;Lee, Min-Jung;Sung, Hyun-Jung;Moon, Jun-Hwan;Song, Seung-Hyun;Lee, Hyung-Keun;Choi, Ji-Hoon;Park, Cheon-Hyoung;Kim, Yoon-Jung;Kim, Jin-Hyuk US2018/86709, 2018, A1 Location in patent:Paragraph 0205-0207

624-65-7 Synthesis