1-(2-Methoxyphenyl)piperazine → 4-[4-(2-Methoxyphenyl)piperazin-1-yl]-1,2-diphenylbutan-1-one

HRID 496895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496895
[C:1]([CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][CH:11]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[Na].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:11][CH2:10][CH:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:29][CH2:28]1

Komponenten

6

Edukt 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 5360545SodiumHCID 12018120HCID 12018120, Verbindung

Produkt 1

HCID 155240254-[4-(2-Methoxyphenyl)piperazin-1-yl]-1,2-diphenylbutan-1-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The 3-benzoyl-3-phenylpropionaldehyde residue obtained from Step B, above, (˜8.85 mmol) was dissolved in 110 mL of methylene chloride. To this solution was added 2-methoxyphenylpiperazine (10.61 mmol) and sodium triacetoxyboranehydride, NaBH(OAc)3, (10.61 mmol). The mixture was stirred at room temperature for 3 hours. Aqueous workup followed by flash chromatography gave pure product 1-(2-methoxyphenyl)-4-[3-(benzoyl)-3-(phenyl)propyl]piperazine (3.48 g) in 95% yield for last two steps. One equivalent of oxalic acid was added to the free base dissolved in methanol. The solvent was evaporated and the product was dried under vacuum to form the oxalate salt.

Quellen und Nachweise

ORD-Eintrag
ord-03b5586918d54d66b24e78fd0628188f
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06946579B2

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