Dimethylamine → N,N-Dimethyl-[5-(9-fluorenone-2-carbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

HRID 611339

Reaktionsgleichung

Reaktionsgleichung von HRID 611339
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[CH:11]1[CH:16]=[C:15]2[C:17]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][C:18]=3[C:19](=[O:20])[C:14]2=[CH:13][CH:12]=1.[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>ClCCl>[CH3:28][N:30]([CH2:33][C:3]1[O:2][C:10]2[CH2:9][CH2:8][N:7]([C:25]([C:22]3[CH:23]=[CH:24][C:17]4[C:15]5[C:14](=[CH:13][CH:12]=[CH:11][CH:16]=5)[C:19](=[O:20])[C:18]=4[CH:21]=3)=[O:27])[CH2:6][C:5]=2[CH:4]=1)[CH3:31]

Komponenten

8

Edukt 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 69913Fluorenone-2-carboxylic acidHCID 76257Diethyl cyanophosphonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Produkt 1

HCID 19600062N,N-Dimethyl-[5-(9-fluorenone-2-carbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.246 g (1.1 mmol) of 9-fluorenone-2-carboxylic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. After the solvent was distilled off under reduced pressure, water was added, followed by 2 extractions with ethyl acetate. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was dissolved in 10 ml of acetic acid; 0.135 ml (1.50 mmol) of 50% aqueous dimethylamine and 0.122 ml (1.50 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with ethyl acetate 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1) to yield the desired product.

Aufarbeitung

  1. temperaturecooling
  2. distillationAfter the solvent was distilled off under reduced pressure, water
  3. additionwas added
  4. extractionfollowed by 2 extractions with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  9. stirringby stirring at 100° C. for 60 minutes
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. extractionextracted with ethyl acetate 2 times
  12. washThe combined organic layer was washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent was distilled off under reduced pressure
  15. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-b0377a86fe2b44abafe21df271341c3f
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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