Tetrahydrofuran → 1-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

HRID 74561

Reaktionsgleichung

Reaktionsgleichung von HRID 74561
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:39]CC1>>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:11]2[C:2]([Cl:1])=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=3)([OH:39])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 836472-Chloro-6-methoxyquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

Produkt 1

HCID 581811261-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under an argon atmosphere 5.0 g (25 mmol) 2-chloro-6-methoxyquinoline in a small amount of THF were added dropwise at −78° C. to 14 mL (28 mmol) of a 2 M lithium diisopropylamide solution (in THF) in 50 mL THF. Then the mixture was stirred for 1.5 h at −78° C. and 4.5 mL (25 mmol) N-benzylpiperidone was added dropwise. The mixture was stirred for a further 15 min with cooling before slowly being heated to RT. The reaction mixture was stirred overnight, evaporated down and purified by flash chromatography on aluminium oxide. The product-containing fractions were combined and evaporated down.

Aufarbeitung

  1. stirringThe mixture was stirred for a further 15 min
  2. temperaturewith cooling
  3. temperaturebefore slowly being heated to RT
  4. stirringThe reaction mixture was stirred overnight
  5. customevaporated down
  6. custompurified by flash chromatography on aluminium oxide
  7. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-9443c894840b43aa8c4008ecd5502c39
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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