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Sodium Bicarbonate → 1-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidine

HRID 1837760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1837760
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:12]1([CH2:18][O:19][C:20]2[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=2[O:22][CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:27]2[CH2:26][CH2:25][CH:24]([CH2:23][O:22][C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[O:19][CH2:18][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:29][CH2:28]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 135677575-Chloro-2-methoxynicotinaldehydeHCID 178378784-[2-(Cyclohexylmethyloxy)phenoxymethyl]piperidine

Produkt 1

HCID 226783551-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

150 mg of 5-chloro-2-methoxy-3-pyridinecarboxaldehyde and 291 mg of 4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidine were dissolved in 5 ml of 1,2-dichloroethane. To the mixture were added 0.06 ml of acetic acid and 214 mg of sodium triacetoxyborohydride, followed by stirring at room temperature overnight. An aqueous saturated sodium bicarbonate was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 285 mg of the title compound as a pale yellow oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-3d74263829e44d8b98bb18325e81d0f6
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06784192B2

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