Acetic Acid → 7-(1-Cyclopropylmethyl-piperidin-4-yloxy)-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

HRID 506748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506748
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:20]=[C:19]3[C:11]([N:12]4[C:17](=[CH:18]3)[C:16](=[O:21])[NH:15][CH2:14][CH2:13]4)=[N:10][CH:9]=2)[CH2:3][CH2:2]1.O.[CH:23]1([CH:26]=O)[CH2:25][CH2:24]1.C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:23]1([CH2:26][N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8]3[CH:20]=[C:19]4[C:11]([N:12]5[C:17](=[CH:18]4)[C:16](=[O:21])[NH:15][CH2:14][CH2:13]5)=[N:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:25][CH2:24]1

Komponenten

8

Edukt 6

HCID 176Acetic AcidHCID 962WaterHCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 684660687-(piperidin-4-yloxy)-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

Produkt 1

HCID 166791247-(1-Cyclopropylmethyl-piperidin-4-yloxy)-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-oneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 0.40 g (1.40 mmol) 7-(piperidin-4-yloxy)-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one in 8 mL tetrahydrofuran, 30 μL (30 μg, 1.67 mmol) water, 0.16 mL (0.15 g, 2.11 mmol) cyclopropanecarboxaldehyde, 0.24 mL (0.25 g, 4.2 mmol) acetic acid and 2.1 mL (1.93 g, 2.1 mmol) sodium cyanoborohydride (1M solution in tetrahydrofuran) were added successively and the reaction mixture was stirred for 18 hours at 55° C. After cooling to room temperature the reaction was poured on 10% aqueous sodium bicarbonate solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant to give 0.19 g (40%) of the desired compound as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the reaction
  2. extractionwas extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-6bc3141338324e60a8a270f62cf5f39e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786109B2

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