反应 #1707

反应方程式

Compound 1

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

benzyl amine

→

Compound 12

收率 97.7%

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

收率 97.7%

溶剂

benzene

反应条件

后处理

1. 1
   温度to reflux under azeotropic conditions
2. 2
   其他After the calculated amount of water was collected
3. 3
   温度the reaction was cooled
4. 4
   浓缩concentrated in vacuo
5. 5
   workup.ADDITIONadded to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL)
6. 6
   温度cooled
7. 7
   浓缩concentrated 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
    其他The layers were separated
11. 11
    萃取extracted with methylene chloride (2×)
12. 12
    洗涤washed with brine
13. 13
    干燥dried over anhydrous magnesium sulfate
14. 14
    过滤filtered
15. 15
    浓缩concentrated in vacuo

实验过程

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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