ChemicalBook CAS DataBase List 3-(4-methoxyphenoxy)propan-1-amine

3-(4-methoxyphenoxy)propan-1-amine synthesis

4synthesis methods

Product Name:3-(4-methoxyphenoxy)propan-1-amine
CAS Number:100841-00-7
Molecular formula:C10H15NO2
Molecular Weight:181.23

63815-39-4 Synthesis

63815-39-4
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100841-00-7
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Yield:100841-00-7 79%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;toluene

Steps:

P.2 Synthesis of 3-(4-methoxyphenoxy)propylamine
PREPARATIVE EXAMPLE 2 Synthesis of 3-(4-methoxyphenoxy)propylamine Under an argon atmosphere, 3-(4-methoxyphenoxy)propionitrile (5.0 g) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise at 80°C for 10 minutes. After stirring for 3 hours at the same temperature, the reaction liquor was returned to room temperature. In an ice-cold bath, a 4 N aqueous sodium hydroxide solution (30 mL) was added for 10 minutes. After 10 minutes, the mixture was stirred at room temperature for 5 minutes, and then stirred at 80°C for 12 hours. The mixture was returned to room temperature, and toluene (100 mL) was added, and the mixture was stirred for 1 hour, and then insoluble material was removed using Celite. An organic layer was isolated, and washed with water (100 mL x 2 times) and saturated brine (100 mL), and then dried over anhydrous sodium sulfate (80 g). The resultant was filtered, and then the filtrate was concentrated under reduced pressure to obtain a white solid (4.0 g, 79.0%). ¹H-NMR (400MHz, CD₃OD) δ: 2.05 (quintet, J=7Hz, 2H), 3.07(t, J=7Hz, 2H), 3.71(s, 3H), 4.01(t, J=6Hz, 2H), 6.79-6.85(m,4H).

References:

Kowa Company, Ltd. EP1852426, 2007, A1

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