Isopropylamine → Ethyl 2-((propan-2-yl)amino)acetate

Propan-2-amine (2001) (59 g, 1.0 mol) and ethyl chloroacetate (122 g, 1.0 mol) were dissolved in toluene (200 mL) and the mixture was stirred at reflux for 2 h. The reaction mixture was allowed to cool to RT, poured into ice-water (500 mL) and extracted with ethyl acetate (3×250 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (10-50% EA/PE) to afford the product, ethyl 2-(isopropylamino)acetate (2002) (70 g, 51% yield) as an oil.

1. temperatureat reflux for 2 h
2. extractionextracted with ethyl acetate (3×250 mL)
3. washThe combined organic layer was washed with brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customthe residue was purified by flash column chromatography on silica gel (10-50% EA/PE)

ORD record

ord-ab9fcff454e04437b39a4eab86ed6476

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569323B2