ChemicalBook CAS DataBase List 4-Methoxyphenethylamine

4-Methoxyphenethylamine synthesis

8synthesis methods

Product Name:4-Methoxyphenethylamine
CAS Number:55-81-2
Molecular formula:C9H13NO
Molecular Weight:151.21

104-47-2 Synthesis

104-47-2
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$6.00/10g

55-81-2
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$39.96/5g

Yield:55-81-2 96%

Reaction Conditions:

with aluminum (III) chloride;lithium aluminium tetrahydride in diethyl ether at 0 - 20;

Steps:

2-(4-Methoxyphenyl)ethanamine (4)
A solution of AlCl3 (6.70 g, 50 mmol) in anhydrous Et2O (50 mL)was added to LiAlH4 (5.70 g, 150.0 mmol) at 0 °C. The resultingmixture was stirred at 0 °C for 10 min. A solution of 2-(4-methoxyphenyl)acetonitrile (3; 10.00 g, 68.0 mmol) in anhydrous Et2O (15mL) was added to the mixture at 0 °C. The reaction mixture wasstirred overnight at r.t. The mixture was diluted with Et2O (25 mL)and quenched with H2O (100 mL). After acidifying the solutionwith concd H2SO4, it was basified with aq 6 M NaOH. The layerswere separated and the aqueous layer was extracted with Et2O(3 × 25 mL). The combined organic layers were washed with brine(2 × 25 mL), dried (MgSO4), filtered, and concentrated under reducedpressure to afford 4 (9.86 g, 65.3 mmol, 96%) as a white crystallinesolid; mp 113-115 °C.

References:

Smith, Keith;El-Hiti, Gamal A.;Alshammari, Mohammed B. [Synthesis,2014,vol. 46,# 3,art. no. SS-2013-Z0717-OP,p. 394 - 402]

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