Dimethylamine → ((1H-imidazol-2-yl)methyl)dimethylamine

Temperature

50 °C

To a two-necked round-bottomed flask equipped with a reflux condenser and a pressure-equalizing addition funnel, was added 2-imidazolecarboxaldehyde (6 g, 62.5 mmol) in MeOH (60 mL). To this suspension (ambient temperature) was added a solution of dimethylamine (40% aqueous, 60 mL) at a fast dropping rate (20 min). After the addition was complete, solid sodium borohydride (7 g, 186.8 mmol,) was CAUTIOUSLY added portionwise over 45 min. Foaming occurred after each portion, and the internal temperature was allowed to maintain ˜50° C. without external cooling. The reaction mixture was then heated to 65° C. for 3 h and allowed to cool to ambient temperature for overnight. The reaction contents were concentrated in vacuo and the resultant residue was taken up in EtOAc (2×30 mL) washed with brine and with CHCl3 (4×100 mL). The EtOAc extract was discarded. The CHCl3 extract was dried over (NaSO4), filtered, and concentrated in vacuo to give 3.7 g of the desired product as a waxy solid.

1. customTo a two-necked round-bottomed flask equipped with a reflux condenser and a pressure-equalizing addition funnel
2. additionAfter the addition
3. temperatureThe reaction mixture was then heated to 65° C. for 3 h
4. temperatureto cool to ambient temperature for overnight
5. customThe reaction contents
6. concentrationwere concentrated in vacuo
7. washwashed with brine and with CHCl3 (4×100 mL)
8. extractionThe EtOAc extract
9. extractionThe CHCl3 extract
10. dry with materialwas dried over (NaSO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-7ead4d37872740fbb68ab6b8c7dcd047

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278971B2