Acetic Acid → 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one

HRID 1943029

Reaktionsgleichung

Reaktionsgleichung von HRID 1943029
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]=O)[C:3]1=[O:14].[CH2:15]([N:22]1[CH2:26][CH2:25][C:24]([CH3:28])([NH2:27])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:15]([N:22]1[CH2:26][CH2:25][C:24]([NH:27][CH2:12][C:4]2[C:3](=[O:14])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)([CH3:28])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 105118971-Benzyl-3-methylpyrrolidin-3-amine

Produkt 1

HCID 584159153-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (956 mg, 5.11 mmol), 1-benzyl-3-methylpyrrolidin-3-amine (972 mg, 5.11 mmol), and acetic acid (0.877 ml, 15.32 mmol) were combined in CH2Cl2 (25 ml) and stirred for 30 min. Sodium triacetoxyborohydride (3248 mg, 15.32 mmol) was added and the reaction stirred for 2.5 hours before being partitioned between CH2Cl2 and satd. bicarb. The aqueous portion was extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was carried on crude.

Aufarbeitung

  1. stirringthe reaction stirred for 2.5 hours
  2. custombefore being partitioned between CH2Cl2 and satd
  3. extractionThe aqueous portion was extracted 3×CH2Cl2
  4. dry with materialthe organic portion dried (Na2SO4)
  5. concentrationthen concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd05b3504fec40c392b54907932d2357
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389720B2

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