Ammonium formate → (2-Amino-5-ethyl-4-fluorophenyl)-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

HRID 2064184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064184
[CH:1]([C:3]1[C:4]([F:25])=[CH:5][C:6]([N+:22]([O-])=O)=[C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH:8]=1)=[CH2:2].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:22][C:6]1[CH:5]=[C:4]([F:25])[C:3]([CH2:1][CH3:2])=[CH:8][C:7]=1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([CH:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH2:14][CH2:15]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 59850136N-(5-Ethenyl-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Produkt 1

HCID 59850156(2-Amino-5-ethyl-4-fluorophenyl)-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N-(5-ethenyl-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D79, 300 mg, 0.86 mmol) and ammonium formate (536 mg, 8.6 mmol) in methanol (50 ml), under argon, was treated with 10% Pd—C, then stirred overnight at room temperature. The mixture was filtered through a celite pad and the solvent evaporated under vacuum. The residue was dissolved in dichloromethane Na2SO4 and concentrated under vacuum to leave 230 mg of title compound as a brown oil (83% yield).

Aufarbeitung

  1. filtrationThe mixture was filtered through a celite pad
  2. customthe solvent evaporated under vacuum
  3. dissolutionThe residue was dissolved in dichloromethane Na2SO4
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a3ee12a422e240afbdb7ee8099a8323f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288412B2

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