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Dimethylformamide → Methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetate

HRID 253602
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 253602
Cl.[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 668619713-((3-Methoxypropoxy)(phenyl)methyl)piperidine hydrochloride

Produkt 1

HCID 57786482Methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-((3-Methoxypropoxy)(phenyl)methyl)piperidine HCl salt (63 mg, 0.212 mmol) was mixed with methyl bromoacetate (20 μL), K2CO3 (75 mg, 2.5 equiv.), and anhydrous DMF (3 mL). The mixture was stirred overnight at rt. LC-MS indicated the reaction was complete. The mixture was diluted with EtOAc and washed with water. The water layer was extracted with EtOAc. The combined organic layers were washed with water and brine, and dried over Na2SO4. After concentration, the residue was purified by flash chromatography on a 4-g silica gel cartridge eluted with a 0-10% methanol in dichloromethane gradient to afford methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetate (19 mg, 27% yield). LC-MS (3 min) tR=1.07 min, m/z 336 (M+1).

Aufarbeitung

  1. washwashed with water
  2. extractionThe water layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography on a 4-g silica gel cartridge
  7. washeluted with a 0-10% methanol in dichloromethane gradient

Quellen und Nachweise

ORD-Eintrag
ord-fb7e025a645648d28fba30e78bd34132
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07872028B2

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