Реакция #1707

Уравнение реакции

Compound 1

7-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

benzyl amine

→

Compound 12

Выход 97.7%

N-Benzyl-1-amino-7-(pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalene

Выход 97.7%

Растворители

benzene

Условия реакции

Обработка

1. 1
   Температураto reflux under azeotropic conditions
2. 2
   ДругоеAfter the calculated amount of water was collected
3. 3
   Температураthe reaction was cooled
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   workup.ADDITIONadded to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL)
6. 6
   Температураcooled
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   workup.ADDITIONThe residue was diluted with ethyl acetate
9. 9
   workup.ADDITIONfollowed by the slow addition of 1N hydrochloric acid
10. 10
    ДругоеThe layers were separated
11. 11
    Экстракцияextracted with methylene chloride (2×)
12. 12
    Промывкаwashed with brine
13. 13
    Сушкаdried over anhydrous magnesium sulfate
14. 14
    Фильтрацияfiltered
15. 15
    Концентрированиеconcentrated in vacuo

Методика

A solution of Compound 1 (820 mg, 3.24 mmol) and benzyl amine (354 μL, 3.24 mmol) in benzene (10 mL) was heated to reflux under azeotropic conditions. After the calculated amount of water was collected, the reaction was cooled and concentrated in vacuo. The residue was taken-up into ethanol (5 mL) and added to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL). The reaction was heated to 80° C., stirred for 30 min, cooled and concentrated in vacuo. The residue was diluted with ethyl acetate followed by the slow addition of 1N hydrochloric acid. The layers were separated. The aqueous phase was adjusted to pH 7 with 2N sodium hydroxide and extracted with methylene chloride (2×). The organics were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 5% methanol:methylene chloride) provided 1.09 g of Compound 12 as an oil.

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