Prop-1-yn-1-amine → HCID 19033955, compound
Reaction equation
[C:1]([NH2:4])#[C:2][CH3:3].[C:5](Cl)(=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C(N(CC)CC)C>[C:1]([NH:4][C:5](=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])#[C:2][CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Propynylamine (10.4 ml, 151.2 mmol) was mixed with 150 ml of triethylamine in a round bottom flask immersed in a cold water bath, and vigorously stirred while nonanoyl chloride (27.0 ml, 149.75 retool) was added in portions from a dropping funnel over a 30 minute period. Additional triethylamine (100 ml) was added to facilitate stirring. At the end of the addition, the water bath was removed and the reaction was stirred for 30 minutes, then filtered. The filtrate was stripped down to a yellow solid. The solid was partitioned between ether and aqueous NaOH, requiring a considerable quantity of ether to dissolve. The combined ether extracts were stripped and recrystallized from heptane to give product as a white crystalline solid, 18.12 g, 92.8 mmol, 62% yield; top. 78°-79.5° C.; 1H NMR (CDCl3) ∂0.88 (t, J=6.0 Hz, 3 H), 1.28 (m, 10 H), 1.63 (m, 2 H), 2.19 (t, J= 7.6 Hz, 2 H), 2.22 (t, J=2.7 Hz, 1 H), 4.06 (dd, J=5.2, 2.6 Hz), 5.62 (br s, 1 H); EI mass spectrum m/z 196 (M+H)+.