Hydrochloric Acid → HCID 60207419, compound

To a two necked 25 mL round bottom flask, charged with 3-(2-methoxy-4-nitrophenoxy)-N,N-dimethylpropan-1-amine (0.5 g, 1.96 mmol) from above, 10 mL of methanol followed by sodium borohydride (0.2 g, 4.2 mmol) and 10% Pd/C (0.05 g). The resulting reaction mixture was stirred at ambient temperature for 1 hour. After this time, the reaction mixture was passed through a cellite cartridge to remove Pd/C. The organic solution was concentrated under vacuo to give a brown solid residue. The resulting solid was treated with hydrochloric acid (2 M in ether). After stirring for 10 minutes, the solid which formed was collected by filtration and washed with water (10 mL) and dried under vacuum to afford the corresponding hydrochloride salt of the title product (0.3 g, 60% yield). 1H NMR (400 MHz, d6-DMSO with D2O) δ: 7.07 (1H, m), 6.99 (1H, m), 6.85 (1H, m), 4.04 (2H, m), 3.79 (3H, s), 3.17 (2H, m), 2.77 (6H, s), 2.13 (2H, m). MS m/z: 225.22 [M+H]+.

1. customThe resulting reaction mixture
2. customto remove Pd/C
3. concentrationThe organic solution was concentrated under vacuo
4. customto give a brown solid residue
5. stirringAfter stirring for 10 minutes
6. customthe solid which formed
7. filtrationwas collected by filtration
8. washwashed with water (10 mL)
9. customdried under vacuum

ORD record

ord-0f54b18c73df4f1aa71f2d8e68cb8d53

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680139B2