Synthesis of propargylamine derivatives under the optimized conditions^a.

Entry	Time (h)	R22NH	R1	Yieldb (%)
1	12	Piperidine	H	96
2	15	Morpholine	H	80
3	18	Piperidine	4-Me	75
4	18	Morpholine	4-Me	73
5	16	Piperidine	2-Cl	79
6	18	Morpholine	2-Cl	68
7	18	Morpholine	4-OMe	85
8	16	Piperidine	2-Me	85
9	18	Morpholine	2-Me	73

^aReaction conditions: 1.2 mmol of morpholine, 1 mmol of benzaldehyde, and 1.3 mmol of phenylacetylene.

^bIsolated yields in 4 mL of CHCl₃.