HCID 57514177, compound → 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine

tert-Butyl 2-(3-bromophenyl)-1-(methylamino)propan-2-ylcarbamate (CD3; R1=Me, R4=Me) (0.62 g, 1.8 mmol) was dissolved in 25% TFA in DCM (25 mL) and the mixture was left stirring at RT for 1 h. The mixture was concentrated in vacuo and the residue was redissolved in CHCl3 (20 mL). The solution was washed with 15% NaOH (10 mL) and the aqueous layer was extracted with CHCl3 (3×10 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 0.33 g (76%) of crude 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine as a colorless oil. 1H NMR (CDCl3) δ 7.65 (t, J=1.7 Hz, 1H), 7.41-7.34 (m, 2H), 7.21 (t, J=7.8 Hz, 1H), 2.86 (dd, J=11.7, 0.6 Hz, 1H), 2.64 (dd, J=11.7, 0.6 Hz, 1H), 2.38 (s, 3H), 1.54 (bs, 3H), 1.43 (s, 9H). MS (ESI) m/e 242.9 (M+H)+. The compound was used in the next step without further purification.

1. waitthe mixture was left
2. concentrationThe mixture was concentrated in vacuo
3. dissolutionthe residue was redissolved in CHCl3 (20 mL)
4. washThe solution was washed with 15% NaOH (10 mL)
5. extractionthe aqueous layer was extracted with CHCl3 (3×10 mL)
6. dry with materialThe combined organic layer was dried over MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-9e3b67e9d58244ec9dd19c10eedfc6df

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778980B2