Diethylamine → 2-(Diethylamino)acetamide

2 g of 2-bromoacetamide (0.015 mol) were slowly added to diethylamine (40 mL, 0.387 mol) and the reaction mixture was heated to reflux for 20 h. After cooling to room temperature, the reaction mixture was filtered and precipitate discarded. The filtrate was concentrated under vacuum to result in slightly yellow solid. This solid was dissolved in chloroform (10 mL) and washed with aqueous saturated solution of Na2CO3 (3×10 mL). Combined organic phases were dried over Na2S04. The filtrate was concentrated under vacuum to result in 1.49 g (79% yield) of light yellow solid, which was azeotropically dried with benzene prior to use in the following reactions. 1H NMR (500 MHz, CDCl3, J=Hz): δ 6.19 (2H, s, br, NH2), 3.01 (2H, s, CH2), 2.56 (4H, q, J 7.2, NEt2), 1.04 (6H, t, J 7.3, NEt2). 13C NMR (125.8 MHz, CDCl3): δ 175.6 (C═O), 57.4 (CH2), 48.6, 12.3 (NEt2). HRMS (ESIMS) m/z for C6H15N2O [M+H]+ calcd 131.1184, found 131.0907.

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 20 h
3. filtrationthe reaction mixture was filtered
4. concentrationThe filtrate was concentrated under vacuum
5. customto result in slightly yellow solid
6. washwashed with aqueous saturated solution of Na2CO3 (3×10 mL)
7. customCombined organic phases were dried over Na2S04
8. concentrationThe filtrate was concentrated under vacuum
9. customto result in 1.49 g (79% yield) of light yellow solid, which
10. dry with materialwas azeotropically dried with benzene

ORD record

ord-edf55de0a35e4063ba5fd776250e5a08

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09217002B2