Phenethylamine → 4-chloro-N-(2-phenylethyl)butanamide

To a solution of phenethylamine (2.42 g, 20 mmol) and NaOH (0.88 g, 22 mmol) in DCM/H2O (20 mL/20 mL) was added 4-chloro-butyryl chloride (2.82 g, 20 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 20 min. The mixture was partitioned between DCM (20 mL) and H2O (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give a white solid. This residue was purified with silica gel column (Hexane/EtOAc=3/1 to 1/1) to obtain HJC-1-48 (4.2 g, 93%) as a white solid. 1H NMR (600 MHz, CDCl3) δ 7.32 (t, 2H, J=7.8 Hz), 7.23-7.26 (m, 1H), 7.20 (d, 2H, J=7.8 Hz), 5.46-5.47 (m, 1H), 3.52-3.58 (m, 4H), 2.82 (t, 2H, J=7.2 Hz), 2.31 (t, 2H, J=7.2 Hz), 2.07-2.11 (m, 2H).

1. customThe mixture was partitioned between DCM (20 mL) and H2O (10 mL)
2. customThe organic layer was separated
3. washwashed with brine (10 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a white solid
8. customThis residue was purified with silica gel column (Hexane/EtOAc=3/1 to 1/1)

ORD record

ord-a32028168ab8480fb934388a994bb12b

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328125B2