ChemicalBook CAS DataBase List methyl-(naphthalen-2-ylmethyl)azanium

methyl-(naphthalen-2-ylmethyl)azanium synthesis

6synthesis methods

Product Name:methyl-(naphthalen-2-ylmethyl)azanium
CAS Number:76532-33-7
Molecular formula:C12H13N
Molecular Weight:171.24

939-26-4

76532-33-7

General procedure for the synthesis of N-methyl-2-naphthalenemethylamine from 2-bromomethylnaphthalene: 2-bromomethylnaphthalene (10 g, 43 mmol) was added batchwise to a stirred mixture of 40 wt% aqueous methylamine solution (50 mL, 581 mmol) and THF (50 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was concentrated under vacuum. The concentrated residue was dissolved in ether (Et2O), washed sequentially with 1.0 N NaOH solution and brine, and the organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated to dryness. Purification by silica gel fast column chromatography (eluent ratio from 98:2 to 9:1 CHCl3/methanol containing 5% NH4OH) afforded N-methyl-2-naphthalenemethylamine (3.95 g, 54% yield) as a clear oil. Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 7.85 (m, 3H), 7.79 (s, 1H), 7.49 (m, 3H), 3.94 (s, 2H), 2.53 (s, 3H).

939-26-4
311 suppliers
$5.00/1g

76532-33-7
87 suppliers
$39.00/100mg

Yield:76532-33-7 54%

Reaction Conditions:

with ammonium hydroxide;methylamine in tetrahydrofuran;diethyl ether;chloroform;water

Steps:

38 Preparation of 2-(methylaminomethyl)naphthalene
Preparation 38 Preparation of 2-(methylaminomethyl)naphthalene To a stirred solution of 40 wt% methylamine in H₂O (50 mL, 581 mmole) in THF (50 mL) at 0 °C was added 2-(bromomethyl)naphthalene (10 g, 43 mmole) in one portion. The reaction was allowed to warm to RT and stirred for 16 hr, then was then concentrated under vacuum. The residue was taken up in Et₂O and washed with 1.0 N NaOH then with brine, dried (Na₂SO₄), and concentrated to dryness. Purification by flash chromatography on silica gel (98:2 to 9:1 CHCl₃/methanol containing 5% NH₄OH) gave the title compound (3.95 g, 54%) as a clear oil: ¹H NMR (400 MHz, CDCl₃) δ 7.85 (m, 3 H), 7.79 (s, 1 H), 7.49 (m, 3 H), 3.94 (s, 2 H), 2.53 (s, 3 H).

References:

Affinium Pharmaceuticals, Inc. EP1226138, 2004, B1

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3815-22-3 Synthesis