ChemicalBook CAS DataBase List 1-(4-CHLOROPHENYL)PROPAN-1-AMINE

1-(4-CHLOROPHENYL)PROPAN-1-AMINE synthesis

4synthesis methods

Product Name:1-(4-CHLOROPHENYL)PROPAN-1-AMINE
CAS Number:74788-46-8
Molecular formula:C9H12ClN
Molecular Weight:169.65

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Yield:74788-46-8 520 mg

Reaction Conditions:

with borane-THF in tetrahydrofuran at 80; for 16 h;

Steps:

83.A A) 1-(4-chlorophenyl)propan-1-amine

A) 1-(4-chlorophenyl)propan-1-amine [0828] To a solution of 1-(4-chlorophenyl)propan-1-one (1.69 g) in ethanol (60 mL) were added hydroxylamine hydrochloride (1.39 g) and triethylamine (2.79 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 hr, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 1-(4-chlorophenyl)-N-hydroxypropan-1-imine. To a solution of 1-(4-chlorophenyl)-N-hydroxypropan-1-imine in tetrahydrofuran (100 mL) was added 1.1 M boranetetrahydrofuran complex/tetrahydrofuran solution (27.3 mL), and the mixture was stirred at 80°C for 16 hr. To the reaction mixture was added 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (520 mg). ¹H NMR (300 MHz, CDCl₃) δ 0.85 (3H, t, J = 7.3 Hz), 1.58-1.74 (2H, m), 3.80 (1H, t, J = 7.0 Hz), 7.21-7.40 (4H, m).

References:

EP2848618,2015,A1 Location in patent:Paragraph 0828

6285-05-8 Synthesis