반응 #791263

반응 방정식

sodium hydroxide

3-quinuclidinone hydrochloride

N-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine

cyanoborohydride

→

title compound

N-(1-Azabicyclo[2.2.2]oct-3-yl)-N'-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine

용매

methanol

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONwas added [Kim, et al., J. Org. Chem. 50, 1927 (1985)]
2. 2
   기타A yellow precipitate formed
3. 3
   workup.STIRRINGAfter stirring for 4 days at room temperature
4. 4
   기타the solvent was evaporated
5. 5
   workup.ADDITIONThe residue was mixed with 4:1 chloroform
6. 6
   여과methanol (at 20 mL) and filtered through a plug of basic alumina
7. 7
   기타The filtrate was evaporated
8. 8
   기타the residue was purified by flash chromatography (alumina, 4:1 chloroform:methanol to 100% methanol)

실험 절차

To a solution of 3-quinuclidinone hydrochloride (600 mg, 3.7 mmol) in methanol (15 mL) was added a solution of N-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine (900 mg, 3.7 mmol) in methanol (11 mL) over a one minute period at room temperature. After stirring for 5 to 10 minutes, a solution of zinc modified cyanoborohydride (8.7 mL of 0.50M cyanoborohydride in methanol, 4.4 mmol) was added [Kim, et al., J. Org. Chem. 50, 1927 (1985)]. A yellow precipitate formed. After stirring for 4 days at room temperature, 50% sodium hydroxide (1 mL) was added and the solvent was evaporated. The residue was mixed with 4:1 chloroform:methanol (at 20 mL) and filtered through a plug of basic alumina. The filtrate was evaporated and the residue was purified by flash chromatography (alumina, 4:1 chloroform:methanol to 100% methanol) to give the title compound as the free base which was converted to the fumaric acid salt (fumaric acid/ethanol), mp 205°-208° C.

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