2-(Dimethylamino)ethanol → Butanoic acid, 2-(dimethylamino)ethyl ester

Temperature

0 °C

To a solution of N,N-dimethyl ethanolamine (4.45 g, 0.05 mol) in 140 mL of anhydrous tetrahydrofuran at room temperature under nitrogen was added triethylamine (5.05 g, 0.05 mol) and stirred for 15 min. The reaction mixture was then cooled at 0° C. and isobutyryl chloride (5.5 g, 0.05 mol) in 10 mL of tetrahydrofuran was added dropwise over 20 min. The resulting suspension was allowed to warm to room temperature and stirred overnight. The resulting solution was filtered and the solvent evaporated. The resulting product was then diluted by adding 200 mL of ether and subsequently washed with 10% aqueous NaOH solution, water and brine. After removal of the solvent, the crude product was chromatographed on a silica gel column using chloroform as the eluent to give liquid product (1.44 g, 50%). 1H NMR (CDCI3): δ 4.10 (t, J=5.82 Hz, 2H), 2.50 (m, 3H), 2.21 (s, 6H), 1.11 (s, 3H), 1.08 (s, 3H); MS m/z 159 (M+), 115, 71, 58 (100%), 42.

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. filtrationThe resulting solution was filtered
4. customthe solvent evaporated
5. additionThe resulting product was then diluted
6. additionby adding 200 mL of ether
7. washsubsequently washed with 10% aqueous NaOH solution, water and brine
8. customAfter removal of the solvent
9. customthe crude product was chromatographed on a silica gel column

ORD record

ord-a56716896401455bba2aa217efc348f2

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998496