Diethyl Ether → 2-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-isobutyric acid, dihydrobromide

HRID 1290512

Reaktionsgleichung

Reaktionsgleichung von HRID 1290512
[Br:1][CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C.C(OCC)C>C(#N)C>[BrH:1].[BrH:1].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][C:3]([C:5]3[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 18918561Methyl 2-(4-bromoacetylphenoxy)isobutyrate

Produkt 1

HCID 1317201052-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-isobutyric acid, dihydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

The product from step (i) above (2.00 g) in acetonitrile (10 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (1.04 g) and triethylamine (0.89 ml) in acetonitrile (15 ml) and the mixture stirred overnight. The precipitated solid was removed by filtration and the filtrate evaporated. Purification of the residue by flash chromatography on silica, eluting with 0 to 5% v/v methanol/dichloromethane, gave a yellow gum. Trituration of this gum with diethyl ether gave methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxy]isobutryate, 170 mg, as a white solid: m.p. 88°-90° C.; NMR (d6 DMSO)δ8.15(2H,d), 7.96(2H,d), 6.82(4H,m), 3.92(2H,s), 3.70(3H,s), 3.33(4H,t), 2.63(4H,t), 1.60(6H,s); m/e 398 (M+H)+ ; calculated for C22H27N3O4.0.25H2O: C, 65.8; H, 6.8; N, 10.5. found: C, 65.8 H, 7.1; N, 10.4%.

Aufarbeitung

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated
  3. customPurification of the residue by flash chromatography on silica
  4. washeluting with 0 to 5% v/v methanol/dichloromethane
  5. customgave a yellow gum

Quellen und Nachweise

ORD-Eintrag
ord-3ff2aca72d3145f89c5a3df08b534f28
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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