反応 #72690

反応方程式

1-benzyl-4-methyl-piperidin-3-one

methanol

methylamine

acetic acid

→

title compound

収率 69.0%

(1-Benzyl-4-methyl-piperidin-3-yl)-methyl-amine

収率 69.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe new mixture stirred at room temperature in a sealed tube for 24 h, at which time
2. 2
   その他the reaction was quenched upon addition of 1 N sodium hydroxide (50 mL)
3. 3
   抽出The reaction mixture was then extracted 3×80 mL with ether
4. 4
   乾燥the combined ether layers dried over sodium sulfate (Na2SO4)
5. 5
   濃縮concentrated to dryness in vacuo

実験手順

To a stirred solution of 1-benzyl-4-methyl-piperidin-3-one (2.3 grams, 11.5 mmol), prepared by the methods of Iorio, M. A. and Damia, G., Tetrahedron, 26, 5519 (1970) and Grieco et al., Journal of the American Chemical Society, 107, 1768 (1985), (modified using 5% methanol as a co-solvent), both references are incorporated by reference in their entirety, dissolved in 23 mL of 2 M methylamine in tetrahydrofuran was added 1.4 mL (23 mmol) of acetic acid and the resulting mixture stirred in a sealed tube for 16 hours at room temperature. Triacetoxy sodium borohydride (4.9 grams, 23 mmol) was added and the new mixture stirred at room temperature in a sealed tube for 24 h, at which time, the reaction was quenched upon addition of 1 N sodium hydroxide (50 mL). The reaction mixture was then extracted 3×80 mL with ether, the combined ether layers dried over sodium sulfate (Na2SO4) and concentrated to dryness in vacuo affording 1.7 grams (69%) of the title compound as a white solid. LRMS: 219.1 (M+1).

出典