2,2-Dimethyl-1-[4-(4-nitro-phenyl)-piperazin-1-yl]-propan-1-one → 1-(2,2-Dimethyl-propyl)-4-(4-nitro-phenyl)-piperazine

A solution of 2,2-dimethyl-1-[4(4-nitro-phenyl)-piperazin-1-yl]-propan-1-one (8.0 g, 27.5 mmol) in THF (100 mL) was added dropwise to a solution of borane-dimethylsulfide complex (16 mL, 166 mmol) in THF (100 mL) over 30 minutes and stirred for 3 h at room temperature. The mixture was quenched with saturated ammonium chloride solution (200 mL) and concentrated to remove organic solvents under reduced pressure (<45° C.). The aqueous layer was extracted with ethyl acetate (3×100 mL) then the combined extracts were washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated to dryness to afford 1-(2,2-dimethyl-propyl)-4-(4-nitro-phenyl)-piperazine (6 g, 79%) as a yellow solid.

1. customThe mixture was quenched with saturated ammonium chloride solution (200 mL)
2. concentrationconcentrated
3. customto remove organic solvents under reduced pressure (<45° C.)
4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
5. washthe combined extracts were washed with water (100 mL) and brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated to dryness

ORD record

ord-18f7e4e37b414933985efe06210a5699

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524705B2