Reaction #1483103

Reaction equation

ethanol amine

3

Dodecyl 2-aminopropanoate

sodium bicarbonate

→

64

Yield 95.0%

dodecyl 2-((2-hydroxyethyl)amino)propanoate

Yield 95.0%

Solvents

acetonitrile water

dodecyl 2-(dimethylamino)propanoate hydrochloride

Conditions

Workup

1. 1
   OtherThe solid obtained in the reaction mixture
2. 2
   Filtrationwas filtered under vacuum
3. 3
   Concentrationthe solvent concentrated
4. 4
   workup.ADDITIONdiluted with ethyl acetate/water
5. 5
   workup.STIRRINGstirred for 15 minutes at 25-30° C
6. 6
   OtherThe aqueous and organic layers were separated
7. 7
   Extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
8. 8
   WashThe combined organic layers were washed with brine solution
9. 9
   DryingThe organic layer was dried over Na2SO4
10. 10
    Concentrationconcentrated under vacuum

Procedure

To a stirred solution of 3 (1 g, 3.2 mmol) in acetonitrile/water (5:5 mL) was added sodium bicarbonate (0.262 g 3.2 mmol) and followed by ethanol amine (0.5 mL, 0.5 vol) at 25-30° C. The reaction mixture was stirred for 12 h at RT; the reaction was monitored by TLC. The solid obtained in the reaction mixture was filtered under vacuum, the solvent concentrated, diluted with ethyl acetate/water and stirred for 15 minutes at 25-30° C. The aqueous and organic layers were separated, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 64 (0.9 g, yield: 95%) as a liquid

Source