반응 #938195

반응 방정식

HCl

hydrogen

cis-1-methyl-4-(4-nitrophenoxy)-3-phenylpiperidine

→

cis-4-(4-aminophenoxy)-1-methyl-3-phenylpiperidine dihydrochloride

용매

ether

ether

ethanol

반응 조건

후처리

1. 1
   여과The catalyst is filtered off
2. 2
   농축the filtrate is concentrated in vacuo to a gum
3. 3
   기타This material is chromatographed on silica gel
4. 4
   기타A purified free base is obtained
5. 5
   여과The resulting precipitate is filtered
6. 6
   세척washed with ether
7. 7
   workup.ADDITIONAbsolute ethanol is added until the mixture
8. 8
   기타crystallization
9. 9
   여과The recrystallized solid is filtered
10. 10
    세척washed with cold acetone
11. 11
    건조ether, and dried

실험 절차

A solution of 3.7 g of the free base of cis-1-methyl-4-(4-nitrophenoxy)-3-phenylpiperidine, of Example 7, in 100 ml of absolute ethanol is hydrogenated over 0.37 g of 10% Pd on carbon catalyst at 45 psi of hydrogen and room temperature. Uptake stops after 48 hours. The catalyst is filtered off and the filtrate is concentrated in vacuo to a gum. This material is chromatographed on silica gel using acetone and then 25% methanol/acetone as solvent. A purified free base is obtained and a portion of this material is dissolved in ether and is then added dropwise to a solution of dry HCl in ether. The resulting precipitate is filtered, washed with ether, and is then immediately suspended in boiling ether. Absolute ethanol is added until the mixture grows clear. Scratching of the cold solution causes crystallization to occur. The recrystallized solid is filtered, washed with cold acetone, then ether, and dried to afford a solid (m.p. 226°-227° C. dec.) of cis-4-(4-aminophenoxy)-1-methyl-3-phenylpiperidine dihydrochloride.

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