N-(3,4-Dimethoxyphenethyl)-2-(4-methoxyphenyl)acetamide synthesis

6synthesis methods

Product Name:N-(3,4-Dimethoxyphenethyl)-2-(4-methoxyphenyl)acetamide
CAS Number:4078-65-3
Molecular formula:C19H23NO4
Molecular Weight:329.39

104-01-8 Synthesis

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N-(3,4-Dimethoxyphenethyl)-2-(4-methoxyphenyl)acetamide

4078-65-3
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Yield:4078-65-3 97%

Reaction Conditions:

at 198 - 200; for 4 h;

Steps:

1.1

Synthesis of (R)-6, 7-dihydroxy-l- (p-hydroxyphenylmethyl)- 1,2, 3,4-tetrahydroisoquinoline hydrobromide salt (step 1): Synthesis of N- (3, 4-Dimethoxyphenethyl) (p- methoxyphenyl) acetamide [scheme 3] To p-methoxyphenyl acetic acid (50.4 g, 0.303 mol) in a 50 ml round-bottom flask, 3,4- dimethoxyphenethylamine (51.2 mL, 0.303 mol) was added dropwise. Then, the flask, equipped with a septum, was charged with nitrogen gas. Using the thermostat, the reaction solution was adjusted to the temperature of 198- 200 °C and heated for 4 hours. Completion of the reaction was detected by thin film chromatography. The reaction mixture was cooled to the room temperature, and chloroform (500 mL) was added thereto to dissolve the produced precipitate. The chloroform solution was successively washed with 1 N HC1, 1 N NaHCO3 and saturated brine, dried over anhydrous magnesium sulfate and filtered with a glass filter. The filtrate was vacuum concentrated to give a yellowish solid, which was then dissolved in a minimal amount of chloroform, added with ether (500 mL) and stirred, to obtain a white solid. Such solid was filtered through a Buchner funnel, followed by removing the solvent under reduced pressure, to yield the desired compound, N- (3, 4-Dimethoxyphenethyl) (p- methoxyphenyl) acetamide (96.8 g, 97%) as a white solid. m. p = 117 °C Rf : 0.38 (hexane : ethyl acetate = 0. 5 : 1) 1H-NMR (300MHz, CDC13) 6 6.5-7. 1 (m, 7H), 5.4 (br, 1H), 3.80 (s, 3H), 3.81 (s, 3H), 3.85 (s, 1H), 3.46 (s, 2H), 3.4 (t, 2H), 2. 6 (t, 2H) IR (KBr pellet, cm~l) : 3322,3002, 2942,2845, 1653, 1521,4170 HRMs : m/z calcd for ClgH23NO4 (M+) : 329. 16. Found: 329.01 Anal. calcd for ClgH23NO4 : C, 69.28 ; H, 7. 04 ; N, 4.25. Found: C, 69.26 H, 7.12 ; N, 4.27

References:

WO2003/95426,2003,A1 Location in patent:Page/Page column 41-42

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4693-91-8 Synthesis