Table 1 Starting materials, solvent, reaction conditions and results of the distinct chemical reactions carried out to obtain TAPAm.

TAPAc (1.01)

Ethanolamine (2.98)

DCC (1.02)

DMAP (0.83)

CHCl₃

RT^a

96

A mixture of TAPAm with N,N’-dicyclohexylurea was always isolated (TAPAm cannot be isolated alone from the final mixture)

TAPAc (0.50)

Ethanolamine (1.49)

EDC (0.50)

DMAP (0.40)

CHCl₃

RT^a

27

42/The use of EDC allow the separation of TAPAm from water soluble N,N’-dicyclohexylureas

However, a flash column chromatography is required to obtain pure TAPAm

TAPEs (0.99)

Ethanolamine (33.07)

Ethanolamine

140

15

43/TAPAm was obtained after recrystallization with ethanol (× 2)

Easy to scale-up

TAPEs (3.14)

Ethanolamine (5.03)

NaOCH₃ (0.31)

Anhydrous toluene

50

22

92/TAPAm was obtained after recrystallization with ethanol (× 2) with a high yield

Easy to scale-up