Methylamine → [(1R)-1-(4-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

Temperature

0 °C

Crude 4-[(2R)-2-(4-Bromophenyl)-2-chloroethyl]morpholine (34.5 g) was dissolved in 200 mL of EtOH at room temperature with magnetic stirring. The resulting solution was cooled to 0° C. and treated with MeNH2 (71 mL, 33 wt % in EtOH) under N2. The reaction flask was capped with a rubber septum and the reaction mixture maintained at room temperature for 48 h. The mixture was then concentrated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated to yield the title compound as a yellow solid (32 g, 93%). MS (ES) m/e 300 [M+H]+.

1. customThe reaction flask was capped with a rubber septum
2. temperaturethe reaction mixture maintained at room temperature for 48 h
3. concentrationThe mixture was then concentrated
4. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
5. washThe organic layer was washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated

ORD record

ord-b226a1d9a7aa484eab93346bd0902f6f

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749998B2