Methylamine → HCID 59277583, compound

To 3-propyl-benzofuran-2-carbaldehyde (1.36 g, 72.2 mmol) was added methylamine (29 mL of a 2 M solution in methanol, 58 mmol). The resulting mixture was stirred overnight at room temperature under nitrogen. The mixture was concentrated under reduced pressure. The residue was taken up in ethanol (20 mL) and the solution was cooled in an ice-bath. NaBH4 (490 mg, 10.8 mmol) was added in one portion. The mixture was concentrated under reduced pressure and the residue taken up in 1 M NaOH. The mixture was extracted with Et2O (3×). The combined organics were washed, dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound (1.68 g, 99%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.60-7.54 (m, 1H), 7.49 (dd, J=7.2, 1.2 Hz, 1H), 7.25-7.20 (m, 2H), 3.76 (s, 2H), 2.65 (t, J=7.2 Hz, 2H), 2.30 (d, J=9.3 Hz, 3H), 1.99 (s, 1H), 1.66-1.58 (m, 2H), 0.94-0.86 (m, 3H); ESI MS m/z 204 (M+H)+.

1. concentrationThe mixture was concentrated under reduced pressure
2. temperaturethe solution was cooled in an ice-bath
3. concentrationThe mixture was concentrated under reduced pressure
4. extractionThe mixture was extracted with Et2O (3×)
5. washThe combined organics were washed
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-cbac9460fbb34d1bbfc2953b67b003fd

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2