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Dimethylamine → N,N-dimethyl-[6-(6-phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 611074
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16]3[CH:19]=[CH:20][O:21][C:15]=3[CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][NH:23][CH3:24].[CH2:25]=O>C(O)(=O)C>[CH3:22][N:23]([CH2:25][C:20]1[O:21][C:15]2[CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:18][CH2:17][C:16]=2[CH:19]=1)[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 154293296-(6-Phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Produkt 1

HCID 19600092N,N-dimethyl-[6-(6-phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.120 g (0.423 mmol) of 6-(6-phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.046 g (0.51 mmol) of 50% aqueous dimethylamine and 0.041 g (0.51 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 15 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

Aufarbeitung

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c4eec27d6d064b17bf84811104e9bd76
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05998433

Notizen zur Reaktion

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