tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate → N-(3-fluorophenyl)piperidin-4-amine

HRID 906340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906340
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

Produkt 1

HCID 4778195N-(3-fluorophenyl)piperidin-4-amineAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 4-[(3-fluorophenyl)amino]-1-piperidinecarboxylate (D3) (2.30 g) in 2M HCl (5 ml) and 1,4-dioxane (40 ml) was heated at 70° C. with stirring overnight. On cooling, the solvent was removed in vacuo and the residue diluted with 2M NaOH solution and extracted with 9:1 EtOAc/tBuOH (×2). The organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (1.33 g). δH (CDCl3, 250 MHz) 7.07 (1H, q), 6.33 (3H, m), 3.83 (1H, br s), 3.33 (1H, br s), 3.12 (2H, m), 2.71 (2H, m), 2.04 (2H, m), 1.30 (2H, m).

Aufarbeitung

  1. temperatureOn cooling
  2. customthe solvent was removed in vacuo
  3. additionthe residue diluted with 2M NaOH solution
  4. extractionextracted with 9:1 EtOAc/tBuOH (×2)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e30d4b3f04b6472faf26622d055f4e34
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012981B2

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