Reacción #1707

Ecuación de reacción

Compound 1

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

benzyl amine

→

Compound 12

Rendimiento 97.7%

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

Rendimiento 97.7%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux under azeotropic conditions
2. 2
   OtroAfter the calculated amount of water was collected
3. 3
   Temperaturathe reaction was cooled
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   workup.ADDITIONadded to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL)
6. 6
   Temperaturacooled
7. 7
   Concentraciónconcentrated 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
    OtroThe layers were separated
11. 11
    Extracciónextracted with methylene chloride (2×)
12. 12
    Lavadowashed with brine
13. 13
    Secadodried over anhydrous magnesium sulfate
14. 14
    Filtraciónfiltered
15. 15
    Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente