Acetic Acid → 8-(1-(cyclopropylmethyl)piperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 506644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506644
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:14]3[N:13]4[CH2:17][CH2:18][NH:19][C:20](=[O:21])[C:12]4=[CH:11][C:10]=3[CH:9]=2)[CH2:3][CH2:2]1.[CH:22]1([CH:25]=O)[CH2:24][CH2:23]1.C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH:22]1([CH2:25][N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8]3[CH:16]=[CH:15][C:14]4[N:13]5[CH2:17][CH2:18][NH:19][C:20](=[O:21])[C:12]5=[CH:11][C:10]=4[CH:9]=3)[CH2:5][CH2:6]2)[CH2:24][CH2:23]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 684610838-(Piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Produkt 1

HCID 166795208-(1-(cyclopropylmethyl)piperidin-4-yloxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-oneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To the solution of 0.27 g (0.95 mmol) 8-(piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one in 6 mL tetrahydrofuran, 20 μL water, 11 μL (99 μg, 1.42 mmol) cyclopropanecarboxaldehyde, 0.16 mL (0.17 g, 2.8 mmol) acetic acid and 1.42 mL (1.42 mmol, 1M solution in tetrahydrofuran) sodium cyanoborohydride were added and the reaction mixture was stirred for 18 hours at 55° C. The mixture was poured on 10% aqueous sodium bicarbonate 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 96 μg (30%) of the desired compound as a white solid.

Aufarbeitung

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. 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-1f92fa6bbe804a9c918f00bda966e38f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786109B2

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