1-Butanol → 4-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Reaktionsgleichung

[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].C([OH:41])CCC>>[C:25]([OH:24])(=[O:41])[C:31]([OH:33])=[O:34].[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Edukt 4

HCID 2631-Butanol

HCID 10340Sodium Carbonate

HCID 68522Benzene, (3-bromopropoxy)-

HCID 27625334-(Diphenylmethylene)piperidine

Produkt 1

HCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Versuchsvorschrift

A mixture of 3.3 g (0.013 mole) of 4-diphenylmethylenepiperidine, 3.3 g (0.015 mole) of (3-bromopropoxy)benzene and 5.3 g (0.05 mole) of anhydrous sodium carbonate in 100 ml of 1-butanol was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between water and benzene. The benzene layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil as residue, the free base of the title compound. The free base was converted to the oxalic acid salt and the solid was recrystallized from absolute ethanol to yield 4.3 g (70%) of the title product as a white powder, m.p. 175°-178° C.