Novel compounds for lightening skin
A compound and composition technology, applied in the field of new compounds, can solve the problems of reducing the effect of hyperpigmentation of the skin
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Embodiment 1
[0131] Example 1 : 4-((cyclohexyl(4-isopropoxyphenyl)methyl)amino)cyclohexanol
[0132]
[0133] 2-Bromopropane (30.2 g, 246 mmol) was added to 4-hydroxybenzaldehyde (20 g, 164 mmol) and potassium carbonate (K 2 CO 3 ) (45.3 g, 328 mmol) in a mixture of N,N-dimethylformamide (DMF) (150 ml), and the mixture was stirred at 50° C., monitored by thin layer chromatography (TLC), until 4 -Hydroxybenzaldehyde disappears completely. The mixture was partitioned between ethyl acetate (EA) (300ml) and water (300ml), and the organic layer was washed with sodium sulfate (Na 2 SO 4 ), filtered and the solvent was removed in vacuo to give crude 4-isopropoxybenzaldehyde (26 g, 96%). A solution of crude 4-isopropoxybenzaldehyde (10 g, 61 mmol) in tetrahydrofuran (THF) (60 ml) was added to cyclohexylmagnesium bromide (12.6 g, 67.1 mmol - prepared from cyclohexyl bromide and magnesium ) in THF (60 ml), and the solution was stirred at room temperature (R.T.) until 4-isopropoxybenzaldehy...
Embodiment 2
[0134] Example 2 : 2-(4-(((4-isopropoxyphenyl)(phenyl)methyl)amino)cyclohexyl)ethanol
[0135]
[0136] 2-Iodopropane (8.2ml, 82mmol) was added to 4-hydroxyphenyl)(phenyl)methanone (5.42g, 27.3mmol) and K 2 CO 3 (18.9 g, 82 mmol) in a mixture of DMF (40 ml), and the mixture was stirred at 90° C. for 2 hours. At this point, TLC showed complete consumption of 4-hydroxyphenyl)(phenyl)methanone. The mixture was partitioned between EA (200ml) and 0.1N sodium hydroxide (NaOH) (200ml), and the organic layer was washed with saturated sodium chloride (NaCl) (200ml), washed with Na 2 SO 4 Drying, filtration and removal of the solvent in vacuo gave crude 4-isopropoxyphenyl)(phenyl)methanone, which was purified by FC to give the pure product as a light yellow oil (6.5 g, 99 %). Sodium borohydride (NaBH 4) (692mg, 18.3mmol) was added portionwise to a solution of 4-isopropoxyphenyl)(phenyl)methanone (4g, 16.6mmol) in methanol (MeOH) (30ml) at 5°C, and stirred at 2 SO 4 Drying, ...
Embodiment 3
[0137] Example 3 : N-((4-isopropoxyphenyl)(phenyl)methyl)-4-methylcyclohexylamine
[0138]
[0139] 4-Methylcyclohexylamine (91 mg, 0.81 mmol) was added to a solution of 1-(chloro(phenyl)methyl)-4-isopropoxybenzene (200 mg, 0.76 mmol) in THF (1 ml) To the solution, TEA (111 ul, 0.80 mmol) was then added, and the solution was stirred at room temperature for 24 hours. At this point TLC showed complete consumption of 1-(chloro(phenyl)methyl)-4-isopropoxybenzene. The reaction mixture was dissolved in 15% IPA in CHCl 3 solution (8ml) and 1N NaOH (8ml), the layers were separated, and the organic layer was washed with saturated NaCl (8ml), washed with Na 2 SO 4 Drying, filtration and removal of solvent in vacuo gave crude N-((4-isopropoxyphenyl)(phenyl)methyl)-4-methylcyclohexylamine which was purified by FC to give pure product , which was a colorless oil (164 mg, 63%). GC-MS showed >98% purity and expected mass (EI ionization) M+ 337.5.
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