Methanol → HCID 11392932, compound

N,N′-Di-n-hexyl L-tartaramide was prepared by the reaction of n-hexyl amine with diethyl L-tartrate. Diethyl L-tartrate (20.007 g, 1.0 eq) and HPLC grade methanol (40 mL) were weighed into a 250 mL round-bottomed flask equipped with a teflon coated magnetic stir bar. n-Hexyl amine (20.614 g, 2.0 eq) was slowly poured into the stirring diethyl L-tartrate solution. Some fuming and a color change from water-white to pale yellow were observed. Additional methanol (10 mL) was used to rinse all of the amine into the reaction flask. The product precipitated after stirring the solution for 30 min at ambient temperature. The white, waxy solid was filtered, washed with methanol (3×30 mL), washed with diethyl ether (2×30 mL), and dried under vacuum. The first crop of product was obtained in 14% yield (4.366 g, 13.80 mmole). A second crop of product was obtained by adding the combined filtrates to 50 mL of water. After filtering, washing with diethyl ether (2×30 mL), and drying under vacuum, 9.382 g of white, waxy solid were obtained. The combined reaction yield was 45%.

1. customequipped with a teflon coated magnetic stir bar
2. washto rinse all of the amine into the reaction flask
3. customThe product precipitated
4. filtrationThe white, waxy solid was filtered
5. washwashed with methanol (3×30 mL)
6. washwashed with diethyl ether (2×30 mL)
7. customdried under vacuum
8. customThe first crop of product was obtained in 14% yield (4.366 g, 13.80 mmole)
9. customA second crop of product was obtained
10. filtrationAfter filtering
11. washwashing with diethyl ether (2×30 mL)
12. customdrying under vacuum, 9.382 g of white, waxy solid
13. customwere obtained
14. customThe combined reaction yield was 45%

ORD record

ord-511d42b29d5d482b9507716c9e69aef4

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399543B1