1,2-Dichloroethane → 2-(4,4-Difluoropiperidin-1-yl)acetyl chloride

HRID 1094715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094715
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[CH2:11][C:12]([OH:14])=O.C(Cl)C[Cl:17]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:2][C:3]1([F:9])[CH2:8][CH2:7][N:6]([CH2:11][C:12]([Cl:17])=[O:14])[CH2:5][CH2:4]1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 27583514,4-Difluoropiperidine hydrochloride

Produkt 1

HCID 598428832-(4,4-Difluoropiperidin-1-yl)acetyl chlorideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4,4-difluoropiperidine hydrochloride (1.44 g, 9 mmol) in DCM (15 mL) was added chloroacetic acid (0.94 g, 10 mmol), TEA (1.5 mL), EDC (3.82 g, 20 mmol) and DMAP (cat.). The reaction mixture was stirred at RT overnight. The contents were transferred to a separatory funnel and DCM layer was washed saturated NaHCO3 solution, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography using 3:1 Pet. Ether:DCM in. 2-(4,4-difluoropiperidin-1-yl)acetyl chloride was isolated as a white solid weighing 1.57 g (yield: 88%).

Aufarbeitung

  1. customThe contents were transferred to a separatory funnel
  2. washDCM layer was washed saturated NaHCO3 solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e773384fbbc44ca39257eae04f47bb2d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133998B2

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