Water → N1-Ethyl-N1,3-dimethylbutane-1,3-diamine

Temperature

70 °C

3-Azido-N-ethyl-N,3-dimethylbutanamide (5.09 g, 27.6 mmol) was dissolved into anhydrous THF (50 mL) and added dropwise to a suspension of LAH (2.10 g, 2.0 equiv, 55.2 mmol) in anhydrous THF (100 mL) to maintain the reaction at reflux (30 min). After complete addition, the flask was fitted with a condenser and the reaction heated in a 70° C. oil bath for 8 h. The reaction mixture was cooled in an ice bath and water (2.1 mL) was added dropwise over 20 min. Then 15% NaOH solution (2.1 mL) was added dropwise over 10 min. The suspension was stirred for a further 10 min and water (2.1 mL) was added in one portion and the mixture stirred for 30 min to a give fine white suspension. The suspension was filtered through a pad of Celite® and washed with diethyl ether (2×100 mL). The combined filtrate was concentrated with a bath temperature between 10-13° C. to an orange liquid (1.87 g, 47%). LRMS (ESI+) for C8H20N2 (144.1); Found: 145 (MH+).

1. temperatureto maintain
2. customthe reaction
3. temperatureat reflux (30 min)
4. additionAfter complete addition
5. customthe flask was fitted with a condenser
6. temperatureThe reaction mixture was cooled in an ice bath
7. stirringthe mixture stirred for 30 min to a give fine white suspension
8. filtrationThe suspension was filtered through a pad of Celite®
9. washwashed with diethyl ether (2×100 mL)
10. concentrationThe combined filtrate was concentrated with a bath temperature between 10-13° C. to an orange liquid (1.87 g, 47%)

ORD record

ord-dfda9b00e4b04442a732adf178acfd95

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2