Table 2.

Condensation reaction of I and II in the presence of CDET/tert-amine with different counter anions.

Entry	Coupling Agent (a)	Counter Anion	Yield (%) (b) (15 min/60 min)
1	CDET/NMM	Cl−	88/91
2	CDET/NMM	ClO4−	57/69
3	CDET/NMM	BF4−	76/78
4	CDET/NMP	Cl−	76/85
5	CDET/NMP	ClO4−	57/59
6	CDET/NMP	BF4−	62/66
7	CDET/MPD	Cl−	79/90
8	CDET/MPD	ClO4−	66/68
9	CDET/TMA	Cl−	83/84
10	CDET/TMA	ClO4−	72/87
11	CDET/NNDP	Cl−	64/69
12	CDET/NNDP	ClO4−	51/70
13	DETMM	ClO4−	71/80
14	DETMM	BF4−	71/73

Reaction conditions: benzoic acid (I): 1.3 mmol, phenylethylamine (II): 1.2 mmol, Solvent: 6 mL methanol, T: 25 °C. ^(a) Coupling agent: 1.3 mmol of CDET and 1.3 mmol of tert-amine were added. ^(b) Yield in III was measured by GLC using mesitylene as internal standard (1.2 mmol).