ChemicalBook CAS DataBase List 1-(2,6-Dimethylphenoxy)-2-propanamine

1-(2,6-Dimethylphenoxy)-2-propanamine synthesis

6synthesis methods

Product Name:1-(2,6-Dimethylphenoxy)-2-propanamine
CAS Number:31828-71-4
Molecular formula:C11H17NO
Molecular Weight:179.26

Mexiletine is 1-methyl-2-(2,2-dimethylphenoxy)ethylamine (18.1.11). Mexiletine is synthesized by reacting the sodium salt of 2,6-dimethylphenol with chloroacetone, forming 1-(2,6-dimethylphenoxy)-2-propanone (18.1.9). Reacting this with hydroxylamine gives the corresponding oxime (18.1.10). Reduction of the oximine group using hydrogen over Raney nickel gives mexiletine (18.1.11).

53012-41-2 Synthesis

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31828-71-4
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Yield:31828-71-4 81%

Reaction Conditions:

with ammonium acetate;sodium cyanoborohydride in methanol at 20; for 96 h;

Steps:

4.1.1.1 Method A
General procedure: Ammonium acetate (23.8g, 310mmol) and sodium cyanoborohydride (1.4g, 21.7mmol) were added to a solution of 1-(2,6-dimethylphenoxy)propan-2-one (3a) (5.5g, 31mmol) in 40mL of MeOH. The reaction mixture was stirred for four days at room temperature. 6M HCl was added dropwise to the mixture reaction to destroy the excess hydride. The organic solvent was removed under vacuum and the residue aqueous phase was made alkaline with NaOH pellets. Then, the aqueous phase was extracted with AcOEt and the combined organic phases were dried (Na₂SO₄). The solvent was evaporated under reduced pressure to give the desired amine ( 1a) as a yellow oil (4.5g, 81%). Spectroscopic data were in agreement with the literature [21].

References:

Roselli, Mariagrazia;Carocci, Alessia;Budriesi, Roberta;Micucci, Matteo;Toma, Maddalena;Di Cesare Mannelli, Lorenzo;Lovece, Angelo;Catalano, Alessia;Cavalluzzi, Maria Maddalena;Bruno, Claudio;De Palma, Annalisa;Contino, Marialessandra;Perrone, Maria Grazia;Colabufo, Nicola Antonio;Chiarini, Alberto;Franchini, Carlo;Ghelardini, Carla;Habtemariam, Solomon;Lentini, Giovanni [European Journal of Medicinal Chemistry,2016,vol. 121,p. 300 - 307]

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