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-1249b81758b14dc1b25c7d4426d18d58

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07126001B2