4-Hexylaniline

clear yellow to red liquid

(3.0g, 16.92mmol) in 9% aqueous solution of sulfuric acid 60mL was dropped slowly, and cooled to 5 . There NaNO2 aqueous solution (3.52g, 51.00mmol) was dropwise 15mL was stirred for 30 minutes at 5 . after that, It was further stirred for 10 hours at room temperature aqueous KI solution (28.08g, 169mmol) After stirring at dropwise 30mL of 0.5 hours 5 of 5 C.. The reaction was quenched with a saturated Na2S2O3 solution, and the reaction product was extracted 3 times with dichloromethane 20 mL. The organic phase was washed with saturated brine, dried over MgSO4, solvent was removed in vacuo after filtration. The concentrated residue was purified by column chromatography (SiO2, eluent: hexane) to give the compound 1 (colorless liquid, 3.59 g, yield: 73%) was obtained.Coupling of long chain aniline with phosphorylated acid. To a stirring solution of the phosphorylated acid (0.252 mmol) in CH2Cl2 (10 mL) was added PyBOP (0. 252 mmol) followed by diisopropylethylamine (0.252 mmol). After 5 minutes of stirring, the aniline (0.252 mmol) was added and stirring was continued for 4 hours. The reaction mixture was then diluted with ethyl acetate (10 mL) and washed with sodium bicarbonate (3 x 10 mL), ammonium chloride (2 x 1 OmL), and the organic layer was dried over sodium sulfate. Solvents were removed under reduced pressure to afford the product.Coupling of long chain aniline with protected serine. To a stirring solution of N-Boc- (D)-Serine-OBn (0.339 mmol) in CH2Ck (10 mL) was added PyBOP (0.339 mmol) followed by diisopropylethylamine (0.339 mmol). After 5 minutes of stirring, the aniline (0.339 mmol) was added and stirring was continued for 4 hours. The reaction mixture was then diluted with ethyl acetate (10 mL) and washed with sodium bicarbonate (3 x 10 mL), ammonium chloride (2 x l OmL), and the organic layer was dried over sodium sulfate. Solvents were removed under reduced pressure to afford a clear gelatinous solid, which was purified by flash chromatography to afford the product.

Molecular Weight:177.29
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:177.151749610
Monoisotopic Mass:177.151749610
Topological Polar Surface Area:26
Heavy Atom Count:13
Complexity:114
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes