Potassium Carbonate → 2-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-Pyran-4-yl}methyl)aniline

{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (300 mg, 0.94 mmol), 2-fluoronitrobenzene (100 μl, 0.95 mmol) and potassium carbonate (150 mg, 1.08 mmol) were stirred together at room temperature in N,N-dimethylformamide (1 ml) for 2 days. The reaction mixture was concentrated in vacuo and the residue partitioned between water (30 ml) and ethyl acetate (100 ml). The layers were separated and the organic phase washed with water (2×20 ml), dried over sodium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow gum (570 mg, 100%). HRMS ESI+ m/z 440.2537 [MH]+.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customthe residue partitioned between water (30 ml) and ethyl acetate (100 ml)
3. customThe layers were separated
4. washthe organic phase washed with water (2×20 ml)
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-bbc7a8f7c7b94b7dba9e34281812d1a4

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456164B2