Potassium Carbonate → Ethyl 2-(4-((6-chloropyridin-3-yl)methyl)piperazin-1-yl)acetate

HRID 79206

Reaktionsgleichung

Reaktionsgleichung von HRID 79206
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][C:19]([CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:20])[CH3:17]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:25]2[CH2:24][CH2:23][N:22]([CH2:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH2:27][CH2:26]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 207112Ethyl piperazine-1-acetate

Produkt 1

HCID 58300204Ethyl 2-(4-((6-chloropyridin-3-yl)methyl)piperazin-1-yl)acetateAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2-chloro-5-(chloromethyl)pyridine (2.0 g, 12 mmol) in acetonitrile (60 mL) was added potassium carbonate (1.5 mL, 25 mmol) followed by 1-(ethoxycarbonylmethyl)piperazine (2.0 mL, 12 mmol). The resulting mixture was stirred at room temperature for 19 h. The mixture was filtered through celite and the filter cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was subjected to combi-flash column chromatography (methanol/DCM with Et3N) to give compound 348 (1.1 g, 30% yield) as a colorless liquid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.31 (1 H, d, J=2.0 Hz), 7.66 (1 H, d, J=6.1 Hz), 7.28 (1 H, d, J=8.1 Hz), 4.18 (2 H, q, J=7.1 Hz), 3.50 (2 H, br. s.), 3.21 (2 H, s), 2.36-2.77 (8 H, m), 1.27 (3 H, t, J=7.2 Hz). LCMS-ESI (POS), M/Z, M+1: Found 298.1.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0dda912a2cf9474aba37226729539639
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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