ChemicalBook CAS DataBase List 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE

4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE synthesis

9synthesis methods

Product Name:4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE
CAS Number:4734-09-2
Molecular formula:C11H17NO
Molecular Weight:179.26

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Yield: 79%

Reaction Conditions:

with sodium tetrahydroborate;nickel(II) chloride hexahydrate in methanol at 0 - 30; for 6 h;Inert atmosphere;Reagent/catalyst;Temperature;

Steps:

1.5; 1.5; 1.7; 1.8; 1.9 Preparation of Compound 4 from Compound 3
5) Add 4-isobutoxybenzonitrile (10g, 57.07mmo1) to a 250mL three-necked flask.Nickel chloride hexahydrate (13.6g, 57.07mmoL), anhydrous methanol 150mL, nitrogen replacement three times, nitrogen protection down temperature to 0 ~ 10 ° C, sodium borohydride (6.5g, 171.2mmo1) was added in batches;6) After the addition is completed, the temperature is slowly raised to 20 to 30 ° C, and the reaction is kept for 6 hours;7) The reaction solution is filtered through celite, and the filtrate is concentrated to remove most of the methanol;8) Add 60 mL of ethyl acetate, slowly add 10% hydrochloric acid to adjust the pH = 1 to 2, adjust the pH to 11~12 with 15% sodium hydroxide solution, and then separate the liquid. The aqueous phase is extracted with 60 mL of ethyl acetate. Phase9) The organic phase was washed once with 60 mL of water and once with 60 mL of brine, dried over anhydrous sodium sulfate, dried and filtered, and the filtrate was evaporated to give 8.6 g of compound, pale yellow liquid, yield 79%

References:

Lizhu Group Xin Beijiang River Pharmaceutical Co., Ltd.;Wang Biao;Chen Xinyao;Xie Weijian;Peng Murong;Chen Yuechang CN108794351, 2018, A Location in patent:Paragraph 0074-0080; 0095-0101; 0113-0119