Sodium Bicarbonate → 1-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrile

HRID 606225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606225
Cl.[C:2]([C:4]1([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].[O:19]=[C:20]1[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][NH:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.ClCCl>[O:19]=[C:20]1[C:25]([CH2:26][N:7]2[CH2:8][CH2:9][C:4]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])([C:2]#[N:3])[CH2:5][CH2:6]2)=[CH:24][CH:23]=[CH:22][NH:21]1

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehydeHCID 222482184-Cyano-4-(2-methylphenoxymethyl)piperidine hydrochloride

Produkt 1

HCID 222484881-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrileAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After then adding 117 mg of the 4-cyano-4-(2-methylphenoxymethyl)piperidine hydrochloride and 70 mg of 2-oxo-1,2-dihydropyridine-3-carboxaldehyde [CAS No. 36404-89-4] to 10 ml of dichloromethane, the mixture was stirred for 20 minutes at room temperature. 139 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate and chloroform. After drying the organic layer over magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (solvent: chloroform/methanol) to obtain the title compound (7 mg, 5% yield).

Aufarbeitung

  1. dry with materialAfter drying the organic layer over magnesium sulfate
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe obtained residue was purified by NH silica gel column chromatography (solvent: chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-dfa5d89d36fb43fdb37e535f73f28d38
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915274B2

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