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With hydrogen; sodium hydroxide; In methanol; water; at 30℃; under 3000.3 Torr;
In a 10L reactor compound of formula II (230 g), methanol (3,7 L), NaOH solution ((123,3) g NaOH is diluted in 460mL water) and Raney Nickel (41 ,193 g) is charged. Reaction mixture is stirred at 30C and 4 bar hb and monitored with HPLC. After reaction is done, it is filtered and solvent is evaporated. To concentrate is added toluene (4,25 L) and water (2,13 L), mixed and separated. To organic phase water is added (2,13 L), pH is adjusted to 2 with 37 % HCI, and phases are separated. To water phase fe/f-butyl methyl ether (2,13 L) is added and pH is adjusted to 10 with 40 % NaOH. Further organic phase is concentrated, ethanol (230 mL) is added, heated to 50C then 4 M HCI in ie/f-butyl methyl ether (355 mL) and ie/f- butyl methyl ether (920 mL). White precipitate started to obtain. Suspension is cooled to room temperature, filtered, washed with ie/f-butyl methyl ether and dried. Product is white solid (256,2, yield 92%).
90%
A mixture of 2-(7-methoxynaphthyl) acetonitrile (100g), methanol (800 ml), aq. sodium hydroxide (30.42 g sodium hydroxide in 100 ml water), 20 g of Raney Ni stirred in hydrogen atmosphere (apply H2 gas up to 10 kg) at 25 to 30 C for 2-3 hrs. Filtered the reaction mixture, distilled out solvent completely under vacuum. IPA is added to the residue and heated at 50 to 55 C, IPA HCI added at 50 to 55 C and stirred for one hour. Cooled the reaction mixture at 10-15C, filtered the solid, washed with IPA and dried. There was thus obtained 2-(7-methoxynanphthyl)ethanamine hydrochloride (Yield 90%, HPLC purity 99.5 to 99.9 %)
83%
Example 2: Preparation of 2-(7-methoxy-l-naphthyi)ethanamine hydrochloride of Formula (D) Methanol (500 ml) was added to an autoclave with 1 Kg/cm2 pressure of Ammonia gas at 10C to 15C and stirred for 1 hour followed by addition of (7-methoxy-l- naphthyl)acetonitrile of Formula (C) (70 g). Raney Nickel (14 g) was added and 5.0 Kg/cm2 pressure of Hydrogen gas was applied at 15C to 25C. The reaction was heated to 50C to 55C. The reaction mass was filtered and treated with ethyl acetate (500 ml) at 25C to 35C and cooled to 0C to 5C followed by addition of Con. HCI acid and maintained for 1 hour. The reaction mass was filtered and washed with chilled ethyl acetate (2 X 50 ml) afforded 2-(7-methoxy- l-naphthyl)ethanamine hydrochloride of formula (D) Yield - 83%
32%
A solution of (7-methoxynaphthalen-l-yl)acetonitrile (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40C. After completion of the reaction, the reaction mixture was filtered through a Hyflo. The filtrate was concentrated under vacuum (200-220 mbar) at 45C to 50C to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10C to 15C to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45C to 50C over 10 to 15 hours to get the title product.Yield (w/w): 32%
32%
A solution of <strong>[138113-08-3](7-methoxynaphthalen-1-yl)acetonitrile</strong> (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40 C. After completion of the reaction, the reaction mixture was filtered through a Hyflo. The filtrate was concentrated under vacuum (200-220 mbar) at 45 C. to 50 C. to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10 C. to 15 C. to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45 C. to 50 C. over 10 to 15 hours to get the title product. Yield (w/w): 32%
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