Aniline → 6-Bromo-N-phenylhexanamide

To a solution of 6-bromohexanoyl chloride (1.00 mL, 6.53 mmol) in THF (35 mL) at 0° C. was added dropwise a solution of aniline (0.60 mL, 6.53 mmol) and TEA (1.09 mL, 7.84 mmol) in THF (5 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 2 h. The mixture was filtered, the solids rinsed with EtOAc, and the filtrate reduced under vacuum. The residue was partitioned between H2O (15 mL) and EtOAc (20 mL) and the layers separated. The aqueous portion was extracted with EtOAc (3×10 mL) and the organic layers combined, washed with HCl (1 N), brine, dried over MgSO4, and filtered. Concentration under reduced pressure left a brown oil which was passed through a plug of silica gel (30% EtOAc/hexanes) under aspiration. Concentration under reduced pressure left 67 as a solid (1.55 g, 5.74 mmol, 88%). TLC Rf 0.36 (25% EtOAc/hexanes); 1H-NMR (400 MHz, DMSO-d6) δ 9.85 (s, 1H), 7.57 (d, 2H), 7.27 (t, 2H), 7.01 (t, 1H), 3.53 (t, 2H), 2.30 (t, 2H), 1.81 (t, 2H), 1.63 (m, 2H), 1.42 (m, 2H); MS (ESI+) calcd for C12H16BrNO 268+270, found 269+271 [M+H]+.

1. filtrationThe mixture was filtered
2. washthe solids rinsed with EtOAc
3. customThe residue was partitioned between H2O (15 mL) and EtOAc (20 mL)
4. customthe layers separated
5. extractionThe aqueous portion was extracted with EtOAc (3×10 mL)
6. washwashed with HCl (1 N), brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationConcentration under reduced pressure
10. waitleft a brown oil which
11. concentrationConcentration under reduced pressure

ORD record

ord-e896d59804c54d2fa594ddbf82a036d3

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06511990B1