반응 #94240

반응 방정식

1,4-benzodioxan-2-yl-acetaldehyde

4-hydroxy-4-phenylpiperidine

hydrogen chloride

2-[2-(4-hydroxy-4-phenylpiperidino)-vinyl]-1,4-benzodioxan

sodium cyanoborohydride

sodium hydroxide

→

2-[2-(4-hydroxy-4-phenylpiperidino)ethyl]-1,4-benzodioxan hydrochloride

용매

methanol

methanol

반응 조건

후처리

1. 1
   기타is formed in situ
2. 2
   농축concentrated to a small volume
3. 3
   workup.ADDITIONdiluted with water
4. 4
   추출The mixture is extracted with ethyl acetate
5. 5
   기타the extract dried
6. 6
   기타evaporated
7. 7
   workup.ADDITIONThe residue is treated with ethanolic hydrogen chloride
8. 8
   기타the precipitate recrystallized from ethanoldiethyl ether

실험 절차

To the solution of 10 g of 1,4-benzodioxan-2-yl-acetaldehyde and 12.7 g of 4-hydroxy-4-phenylpiperidine in 300 ml of methanol is added 8 ml of 4.5 N ethanolic hydrogen chloride at which conditions the 2-[2-(4-hydroxy-4-phenylpiperidino)-vinyl]-1,4-benzodioxan is formed in situ. After standing for one hour, at room temperature the solution of 2.4 g of sodium cyanoborohydride in 30 ml of methanol is added dropwise while stirring. After one hour the solution is made strongly basic with aqueous sodium hydroxide, concentrated to a small volume and diluted with water. The mixture is extracted with ethyl acetate, the extract dried and evaporated. The residue is treated with ethanolic hydrogen chloride and the precipitate recrystallized from ethanoldiethyl ether, to yield the 2-[2-(4-hydroxy-4-phenylpiperidino)ethyl]-1,4-benzodioxan hydrochloride melting at 203°.

출처