Water → Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517560
O1CCCCC1O[CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[CH:10]=1.S(Cl)([Cl:33])=O.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:33][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86711499benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 86711500Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate (7.3 g, 17.7 mmol) in DCM (30 mL), thionyl chloride (7.7 mL, 106.6 mmol) was added slowly at RT, followed by the addition of H2O (0.05 mL). The mixture was stirred at RT overnight, poured into a solution of aqueous NaHCO3 (sat., 50 mL), and extracted with DCM (2×30 mL). The combined organic layers were washed with H2O (50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1) to give benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow solid (5.0 g, 82%). MS (ES+) C18H20ClN3O2 requires: 345, found: 346 [M+H]+.

Aufarbeitung

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic layers were washed with H2O (50 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9cfdcba404f049d4a1eb7c895fafdf2f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115120B2

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