Reaktion #7503

Reaktionsgleichung

NaOH

1-(phenylmethyl)-4-[1-(phenylmethyl)-1H-imidazol-2-yl]-4-piperidinol

AlCl3

AlCl3

→

1′-(phenylmethyl)spiro[imidazo[1,2-b]isoquinoline-10[5H],4′-piperidine]dihydrochloride

Ausbeute 1.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   workup.ADDITIONThe mixture was poured into ice
3. 3
   Extraktionextracted with CH2Cl2
4. 4
   TrocknenThe organic layer was dried (MgSO4)
5. 5
   Filtrationfiltered off
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by HPLC (eluent: CH2Cl2/(CH3OH/NH3) 99/1)
8. 8
   SonstigeThe pure fractions were collected
9. 9
   Sonstigeevaporated

Vorschrift

1-(phenylmethyl)-4-[1-(phenylmethyl)-1H-imidazol-2-yl]-4-piperidinol (0.124 mol) and AlCl3 (0.31 mol) were stirred in a melt at 120° C. for 1 h. The mixture was cooled, AlCl3 (0.31 mol) was added and the mixture was stirred at 120° C. for 1 h. The mixture was poured into ice, alkalized with NaOH 50% and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered off and evaporated. The residue was purified by HPLC (eluent: CH2Cl2/(CH3OH/NH3) 99/1). The pure fractions were collected and evaporated. The residue was converted into the hydrochloric acid salt (1:2) in (C2H5)2O, yielding 0.91 g of 1′-(phenylmethyl)spiro[imidazo[1,2-b]isoquinoline-10[5H],4′-piperidine]dihydrochloride.dihydrate (2%) (interm. 3; mp. 161.2° C.).

Quelle