반응 #94388

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sodium borohydride

sodium borohydride

sodium borohydride

2,3-dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-one, hydrochloride

→

amorphous solid

수율 50.6%

2,3-Dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-ol

수율 50.6%

용매

water

water

water

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise)
2. 2
   workup.STIRRINGThe mixture is stirred for an additional 2 hours at room temperature
3. 3
   온도The reaction mixture is chilled to 0° C.
4. 4
   workup.WAITAfter 30 minutes at 0° C.
5. 5
   기타the solvents are removed in vacuo
6. 6
   건조The organic layer is dried with sodium sulfate
7. 7
   기타evaporated in vacuo to a foamy residue (4.1 g)
8. 8
   workup.DISSOLUTIONThe residue is dissolved in a small amount of dichloromethane
9. 9
   기타chromatographed on a 150 g-Activity III neutral alumina column
10. 10
    기타After evaporation of the combined fractions there

실험 절차

A suspension of 4.9 g of 2,3-dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-one, hydrochloride in 100 ml of methanol is cooled to 0° C. and treated with a solution of 1.52 g of sodium borohydride in 10 ml of water (the sodium borohydride is added dropwise). The mixture is stirred at room temperature overnight followed by the addition of an additional 1.52 g of sodium borohydride in 10 ml of water at 0° C. The mixture is stirred for an additional 2 hours at room temperature. The reaction mixture is chilled to 0° C. and treated with 30 ml of water. After 30 minutes at 0° C., the solvents are removed in vacuo, and the residue is distributed between dichloromethane and water. The organic layer is dried with sodium sulfate and evaporated in vacuo to a foamy residue (4.1 g). The residue is dissolved in a small amount of dichloromethane and chromatographed on a 150 g-Activity III neutral alumina column using ethyl acetate/hexane (3:1) in 50 ml fractions (a total of 500 ml). After evaporation of the combined fractions there is 2.7 g of residue. Trituration with pentane gives 2.28 g of an amorphous solid with indeterminant melting point. Crystallization from ethyl acetate/pentane yields 1.80 g of the title compound, melting point 109.5°-111.5° C.

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