[CH2:1](Cl)[C:2]#[CH:3].[NH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CO>[CH2:1]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:2]#[CH:3]With stirring, a solution of 2-propynyl chloride (40.31 g) in dry methanol (50 ml) was added dropwise to a solution of piperidine (92.14 g) in dry methanol (100 ml). The mixture was stirred at 25° C. for 3 hours and then filtered. The filtrate was concentrated under reduced pressure and the residue was distilled (boiling point: 163–165° C./atmospheric pressure).
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