反応 #1707

反応方程式

Compound 1

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

benzyl amine

→

Compound 12

収率 97.7%

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

収率 97.7%

溶媒

benzene

反応条件

後処理

1. 1
   温度to reflux under azeotropic conditions
2. 2
   その他After the calculated amount of water was collected
3. 3
   温度the reaction was cooled
4. 4
   濃縮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
   濃縮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
    その他The layers were separated
11. 11
    抽出extracted with methylene chloride (2×)
12. 12
    洗浄washed with brine
13. 13
    乾燥dried over anhydrous magnesium sulfate
14. 14
    ろ過filtered
15. 15
    濃縮concentrated in vacuo

実験手順

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.

出典