Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C(Cl)Cl>[CH2:1]([NH:4][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]#[CH:3]
Reactant: C#CCN
Reactant: O=C(Cl)OCc1ccccc1
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: C#CCNC(=O)OCc1ccccc1
Temperature: 25 °C
Reaction time: 2 h
Yield: 56 %

Procedure:
To a solution of propargylamine and triethylamine (1.3 eq.) in DCM (3 M) at 0° C., it was added dropwise a solution of benzyl chloroformate (1.1 eq.) in DCM (5 M). The reaction mixture was stirred at RT for 2 h. After evaporation of the solvent the resulting residue was purified by flash column chromatography on silica (EtOAc/Petroleum ether 1:10) to yield (56%) the title compound. 1H NMR (300 MHz, CDCl3, 300K) δ 7.3 (5H, s), 5.29 (2H, s), 5.0 (1H, bs), 3.85 (2H, d, J=3.3 Hz), 2.21 (1H, m). MS (ES+) C11H11NO2 requires: 189, found: 190 (M+H)+.