Reaction #1328399

Reaction equation

amine hydrochloride

Methyl 6-Aminohexanoate Hydrochloride

ethyl trifluoroacetate

triethylamine

→

product ( 3 )

Yield 87.0%

Methyl 6-(Trifluoroacetamido)hexanoate

Yield 87.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONTo a 2 liter round bottom flask, charged with 100.2 g
2. 2
   Concentrationconcentrated via rotary evaporation
3. 3
   workup.ADDITIONThe residue was diluted with 500 mL of diethyl ether
4. 4
   Filtrationfiltered
5. 5
   WashThe filtrate was washed with 3×300 mL aliquots of 1N aqueous HCl, 200 mL of de-ionized water, 2×200 mL aliquots of saturated aqueous sodium bicarbonate and finally with 200 mL of de-ionized water
6. 6
   DryingThe organic phase was dried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   workup.DISTILLATIONThe residue was distilled under vacuum

Procedure

To a 2 liter round bottom flask, charged with 100.2 g is (0.552 mol) of amine hydrochloride 2 and 1 liter of methanol was added 100 g (0.703 mol) of ethyl trifluoroacetate followed by 120 mL (0.861 mol) of triethylamine. The mixture was stirred at 20–30° C. for 19 h and then concentrated via rotary evaporation. The residue was diluted with 500 mL of diethyl ether and then filtered. The filtrate was washed with 3×300 mL aliquots of 1N aqueous HCl, 200 mL of de-ionized water, 2×200 mL aliquots of saturated aqueous sodium bicarbonate and finally with 200 mL of de-ionized water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was distilled under vacuum to afford 115.8 g of the product (3) as a colorless oil: b.p.=113–116° C. at 120 mm Hg: 1H NMR (d6-DMSO) d 3.57 (3H, s), 2.75 (2H, m), 2.29 (2H, t), 1.60–1.40 (4H, m) and 1.37–1.19 (2H, m) ppm.

Source