反応 #438346

反応方程式

N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

thiophene-2-carboxaldehyde

NaBH3CN

NaBH3CN

→

amine

収率 62.4%

N-(2-pyridinylmethyl)-N′-[2-thiopheneylmethyl]-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

収率 62.4%

溶媒

methanol

反応条件

後処理

1. 1
   その他The solvent was removed under reduced pressure and CH2Cl2 (30 mL) and water (10 mL)
2. 2
   workup.ADDITIONwere added to the residue
3. 3
   その他The phases were separated
4. 4
   抽出the aqueous phase was extracted with CH2Cl2 (3×10 mL)
5. 5
   乾燥The combined organic phases were dried (Na2SO4)
6. 6
   濃縮concentrated
7. 7
   その他Purification of the crude material by radial chromatography on silica gel (2 mm plate, 40:1 CH2Cl2-MeOH)

実験手順

To a stirred solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.280 g, 0.610 mmol) in anhydrous methanol (6 mL), at room temperature, was added thiophene-2-carboxaldehyde (0.25 mL, 2.67 mmol) followed by NaBH3CN (0.081 g, 1.30 mmol) and the resultant solution was stirred at room temperature. After 1 day, an additional amount of NaBH3CN (0.083 g, 1.31 mmol) was added and the solution was stirred at room temperature for an additional 3 days. The solvent was removed under reduced pressure and CH2Cl2 (30 mL) and water (10 mL) were added to the residue. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic phases were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (2 mm plate, 40:1 CH2Cl2-MeOH) provided 0.173 g of the desired amine as a yellow oil.

出典