Reaction #1483107

Reaction equation

dimethyl amine

74

2-methyltridecan-2-yl 2-bromopropanoate

sodium bicarbonate

→

75

Yield 83.4%

2-methyltridecan-2-yl 2-(dimethylamino)propanoate

Yield 83.4%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe solid obtained in the reaction mixture
2. 2
   Filtrationwas filtered under vacuum
3. 3
   ConcentrationThe solvent was 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 74 (2 g, 5.7 mmol) in acetonitrile (10 mL) was added sodium bicarbonate (0.48 g, 5.74 mmol) and followed by dimethyl amine (40% in water) (10 mL, 88.8 mmol) at 25-30° C. The reaction mixture was stirred for 3 hours at 25-30° C.; the reaction was monitored by TLC. The solid obtained in the reaction mixture was filtered under vacuum. The solvent was 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 75 (1.49 g, yield: 83%) as a liquid.

Source