반응 #1707

반응 방정식

Compound 1

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

benzyl amine

→

Compound 12

수율 97.7%

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

수율 97.7%

용매

benzene

반응 조건

후처리

1. 1
   온도to reflux under azeotropic conditions
2. 2
   기타After the calculated amount of water was collected
3. 3
   온도the reaction was cooled
4. 4
   농축concentrated in vacuo
5. 5
   workup.ADDITIONadded to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL)
6. 6
   온도cooled
7. 7
   농축concentrated 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
    기타The layers were separated
11. 11
    추출extracted with methylene chloride (2×)
12. 12
    세척washed with brine
13. 13
    건조dried over anhydrous magnesium sulfate
14. 14
    여과filtered
15. 15
    농축concentrated in vacuo

실험 절차

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.

출처