1-Methyl-aminomethyl naphthalene synthesis
- Product Name:1-Methyl-aminomethyl naphthalene
- CAS Number:14489-75-9
- Molecular formula:C12H13N
- Molecular Weight:171.24
1498015-90-9
14489-75-9
The crude product N-methyl-N-(1-naphthylmethyl)formamide prepared according to step (a) was suspended in 300 mL of 20% aqueous sodium hydroxide solution and the reaction was heated at 60-70°C for 7 hours. Upon completion of the reaction, the mixture was cooled to 25 °C and subsequently extracted with toluene (2 x 200 mL). The toluene extracts were combined and back-extracted with 3N hydrochloric acid (2 x 300 mL). The aqueous phase was decolorized with activated carbon and the pH was adjusted with 20% aqueous sodium hydroxide to 10.0. The released free base was extracted with toluene, and the toluene layers were combined and distilled to remove the solvent to give 86 g of crude product. Finally, 82 g (85% yield) of pure N-methyl-1-naphthalenemethylamine was obtained by high vacuum distillation purification.
3400-33-7
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Yield:14489-75-9 97%
Reaction Conditions:
Stage #1: N-methyl-1-naphthalenecarboxamidewith lithium aluminium tetrahydride in tetrahydrofuran at 0;Heating / reflux;
Stage #2: with water;ammonium chloride in tetrahydrofuran at 0 - 20; for 1 h;
Steps:
1.8
A solution of naphthalene- 1-carboxylic acid methyl amide (0.83 g, 4.40 mmol) in anhydrous tetrahydrofuran (10 mL) was added via a syringe to a stirred suspension of lithium aluminum hydride (0.41 g, 9.68 mmol) in anhydrous tetrahydrofuran (10 mL), at O0C, over 10 minutes under nitrogen. The mixture was heated to reflux overnight, cooled to O0C and quenched with saturated ammonium chloride solution (2 mL). The reaction was allowed to warm to ambient temperature over 1 hour, filtered through a pad of celite, extracted with ether, and the organic layer was dried and concentrated under reduced pressure to give the title compound as a yellow oil (0.75 g, 97%). The material is used directly in the next step without purification. 1H-NMR (CDCl3) δ: 7.40-7.57 (m, 4H), 7.78 (m, IH), 7.87(m, IH), 8.12 (m, IH).
References:
WO2008/73863,2008,A2 Location in patent:Page/Page column 64
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14489-75-9
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