Triethylamine → Dimethyl-[6-(3-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611109
Cl.Cl.[CH3:3][N:4]([CH2:6][C:7]1[O:15][C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:9]=2[CH:8]=1)[CH3:5].[C:16]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH3:5][N:4]([CH3:3])[CH2:6][C:7]1[O:15][C:10]2[CH2:11][N:12]([C:27](=[O:28])[C:26]3[CH:30]=[CH:31][CH:32]=[C:24]([C:16](=[O:23])[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:25]=3)[CH2:13][CH2:14][C:9]=2[CH:8]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 1013863-Benzoylbenzoic acidHCID 19600082N,N-dimethyl-(4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl)amine dihydrochloride

Produkt 1

HCID 19600018Dimethyl-[6-(3-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.228 g (0.900 mmol) of the above N,N-dimethyl-(4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl)amine dihydrochloride, 0.26 g (1.1 mmol) of 3-benzoylbenzoic acid and 0.53 ml (3.8 mmol) of triethylamine in 30 ml of dichloromethane, 0.23 g (1.43 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 2 times. The combined organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (chloroform to chloroform/methanol=50/1) to yield the desired product.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography (chloroform to chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-5999145f45d341858b2d4028ded8cff7
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

Notizen zur Reaktion

Wird geladen…