Formaldehyde → ethyl N-(4-fluoroindol-3-ylmethyl)piperidin-4-ylcarboxylate

HRID 1683859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683859
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C=O.[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2.[C:24](=O)(O)[O-].[Na+]>O1CCOCC1.C(O)(=O)C>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([CH2:24][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)=[CH:18][NH:19]2

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 27745024-Fluoroindole

Produkt 1

HCID 19040931ethyl N-(4-fluoroindol-3-ylmethyl)piperidin-4-ylcarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A stirred solution of 1.8 grams (0.011 mole) of ethyl piperidin-4-ylcarboxylate in 10 mL of dioxane was cooled to 0° C., and 10 mL of acetic acid, followed by 0.9 mL of aqueous 37% formaldehyde were added. To this was then slowly added a solution of 1.5 grams (0.011 mole) of 4-fluoroindole in 10 mL of dioxane. Upon completion of the addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about five hours. After this time the reaction mixture was again cooled to 0° C., and neutralized with an aqueous solution saturated with sodium bicarbonate. The mixture was extracted with two 100 mL portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium chloride, dried with sodium sulfate, and filtered. The filtrate was then passed through a pad of silica gel. The eluate was concentrated under reduced pressure, yielding 1.2 grams of ethyl N-(4-fluoroindol-3-ylmethyl)piperidin-4-ylcarboxylate, mp 96°-105° C. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. additionwere added
  2. additionUpon completion of the addition
  3. temperatureAfter this time the reaction mixture was again cooled to 0° C.
  4. extractionThe mixture was extracted with two 100 mL portions of diethyl ether
  5. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe eluate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82b1ef623e1b457f93a0d69884a7a3dc
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639763

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