4-Iodoaniline → N,N-Dihexyl-4-iodoaniline

Temperature

100 °C

4-Iodoaniline (15.05 g, 6.87×10−2 mol), K2CO3 (19.00 g, 0.137 mol), 1-iodohexane (32.0 ml, 0.217 mol) and dry DMF (170 ml) were added to a 500-ml two-neck round-bottom flask. Ar was bubbled into the reaction mixture for 10 min. The reaction mixture was stirred at 90° C. for 16 h and at 100° C. for 2.5 h under Ar. After cooling, the reaction mixture was filtered to remove inorganic solids. Solvents were removed in vacuo, and water was added to the reaction mixture. The organic layers were extracted with CHCl3, washed with aq. NaHCO3 and water, and dried over Na2SO4. The residue was chromatographed on silica gel 4:1 hexane:CHCl3 as the eluent. Yield=20.47 g (77% based on 15.05 g of 4-iodoaniline). 1H NMR (250 MHz, CDCl3): δ 7.41 (d, 2H, J=8.8 Hz, Ph), 6.40 (d, 2H, J=9.1 Hz, Ph), 3.20 (t, 4H, J=7.6 Hz, —NCH2—), 1.43-1.61 (m, 4H, —NCH2CH2—), 1.18-1.37 (m, 12H, —CH2—), 0.89 (t, 6H, J=6.5 Hz, —CH3). CI MS m/z: 388.149 ((M+H)+) (calcd 388.150).

1. customAr was bubbled into the reaction mixture for 10 min
2. temperatureAfter cooling
3. filtrationthe reaction mixture was filtered
4. customto remove inorganic solids
5. customSolvents were removed in vacuo, and water
6. additionwas added to the reaction mixture
7. extractionThe organic layers were extracted with CHCl3
8. washwashed with aq. NaHCO3 and water
9. dry with materialdried over Na2SO4
10. customThe residue was chromatographed on silica gel 4:1 hexane

ORD record

ord-38a49293b9f347d1abc51bc5521e2357

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842758B2