Triethylamine → 4-[2-[4-(4-Pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetic acid monohydrochloride

HRID 1290537

Reaktionsgleichung

Reaktionsgleichung von HRID 1290537
[N:1]1([CH2:8][C:9]([C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:13][CH:12]=2)=[O:10])[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl.[Cl:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>O.O1CCOCC1>[ClH:24].[N:28]1[CH:29]=[CH:30][C:25]([N:4]2[CH2:5][CH2:6][N:1]([CH2:8][C:9]([C:11]3[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=3)=[O:10])[C:2](=[O:7])[CH2:3]2)=[CH:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 18918321Methyl 4-[2-(piperazin-2-one-1-yl)acetyl]-phenoxyacetate

Produkt 1

HCID 700791174-[2-[4-(4-Pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetic acid monohydrochlorideAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of methyl 4-[2-(piperazin-2-one-1-yl)acetyl]phenoxyacetate (0.347 g), 4-chloropyridine hydrochloride (0.19 g) and triethylamine (0.178 g) in water (8 ml) and dioxan (1 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was triturated with water (2 ml) and filtered. The solid thus obtained was recrystallised from water to give the title compound (0.187 g), m.p. 275°-277° C.; NMR (d6DMSO) δ 8.33(2H, d), 8.0(2H,d), 7.21(2H,d), 7.1(2H,d), 4.97(2H,s), 3.94(2H,m), 3.59(2H,m); m/e 370(M+H+ ; calculated for C19H20N3O5Cl.0.75 H2O: C, 54.4; H, 5.0; N, 10.0. Found: C, 54.5H, 5.3; N, 9.5%.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was triturated with water (2 ml)
  3. filtrationfiltered
  4. customThe solid thus obtained
  5. customwas recrystallised from water

Quellen und Nachweise

ORD-Eintrag
ord-98233bb25fe0411b94eb04fb3be43b34
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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