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Hydrochloric Acid → Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylate

HRID 1963260
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1963260
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31].Cl>ClCCl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][N:9]2[C:29]([O:30][CH3:31])=[O:32])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731797Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylate

Produkt 1

HCID 86646603Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylateAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylate (3.89 g, 14.65 mmol) was dissolved in dichloromethane (150 mL). DIPEA (3.06 mL, 17.58 mmol) was added, followed by methyl carbonochloridate (1.615 mL, 20.51 mmol). The mixture was stirred at room temperature for 2 h. 0.1 HCl and DCM were added. The phases were separated and the aqueous phase was extracted with DCM. The combined organic layers were washed with satd NaHCO3, filtered through a phase separator and evaporated. Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylate (3.19 g, 67%) was isolated. MS m/z 324 (M+H)+

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe combined organic layers were washed with satd NaHCO3
  4. filtrationfiltered through a phase separator
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e81b0c7efe2a425cbc46cbe412d00f67
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415378B2

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