Реакция #438359

Уравнение реакции

benzyl bromide

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

K2CO3

→

desired product

Выход 60.6%

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

Выход 60.6%

Растворители

CH3CN

Условия реакции

Обработка

1. 1
   Концентрированиеthe reaction mixture was concentrated
2. 2
   Другоеthe residue was partitioned between CH2Cl2 (10 mL) and water (5 mL)
3. 3
   ДругоеThe phases were separated
4. 4
   Экстракцияthe aqueous phase was extracted with CH2Cl2 (2×10 mL)
5. 5
   СушкаThe combined organic extracts were dried (Na2SO4)
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеPurification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH)

Методика

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.220 g, 0.390 mmol) in CH3CN (8 mL), at room temperature, was added powdered K2CO3 (0.153 g, 1.11 mmol) followed by excess benzyl bromide (0.20 mL, 1.68 mmol). After 18 hours, the reaction mixture was concentrated and the residue was partitioned between CH2Cl2 (10 mL) and water (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography (2 mm plate, 20:1 CH2Cl2—CH3OH) provided the desired product (0.106 g, 44%) as a white solid.

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