Ethyl Acetate → (S)-4-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzo(b)furan-2-yl methyl ketone maleate

HRID 460636

Reaktionsgleichung

Reaktionsgleichung von HRID 460636
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH3:17][C:18]([C:20]1[O:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[CH:21]=1)=[O:19].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].C([O:40][CH2:41][CH3:42])(=O)C>>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[CH3:17][C:18]([C:20]1[O:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([O:33][CH2:32][C@@H:41]([OH:40])[CH2:42][N:14]3[CH2:15][CH2:16][CH:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH2:12][CH2:13]3)[C:22]=2[CH:21]=1)=[O:19]

Komponenten

5

Edukt 4

HCID 8857Ethyl AcetateHCID 154352-AcetylbenzofuranHCID 444266Maleic AcidHCID 220292644-(Naphthalen-2-yl)piperidine

Produkt 1

HCID 69497711(S)-4-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzo(b)furan-2-yl methyl ketone maleate

Versuchsvorschrift

By the reactions in the same manner as in Example 3 using (S)-4-glycidyloxybenzo(b)furan-2-yl methyl ketone (0.52 g) obtained in Starting Material Synthesis Example 71 and 4-(naphthalen-2-yl)piperidine (0.47 g), (S)-4-(2-hydroxy-3-(4-naphthalen-2-yl)piperidino)propyloxy)benzo(b)furan-2-yl methyl ketone (0.87 g) was obtained as a brown oil. This was dissolved in ethyl acetate and maleic acid (0.22 g) was added. The precipitated crystals were recrystallized from a mixed solvent of isopropanol-ethyl acetate to give the title compound (0.76 g) as pale-yellow crystals, melting point 153–155° C.

Aufarbeitung

  1. customwas obtained as a brown oil
  2. customThe precipitated crystals were recrystallized from a mixed solvent of isopropanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0fc6302ec1ee4ea392d094007397ede9
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196199B2

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