Trifluoroacetic acid → N-[4-Fluoro-3-(methyloxy)phenyl]-4-piperidinamine

HRID 883767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883767
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:4][C:3]=1[O:22][CH3:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:4][C:3]=1[O:22][CH3:23]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 576995241,1-Dimethylethyl 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-1-piperidinecarboxylate

Produkt 1

HCID 57699516N-[4-Fluoro-3-(methyloxy)phenyl]-4-piperidinamineAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-1-piperidinecarboxylate (D9) (1.45 g, 4.48 mmol) in DCM (16 ml) was cooled in an ice bath and TFA (4 ml) was added. The reaction mixture was stirred for 1 h, then warmed to room temperature and stirred for 2 h. The solvent was removed in vacuo and the residue partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic phase was washed with further saturated aqueous NaHCO3 solution. The aqueous was concentrated to ˜50% volume, further basified with 2M NaOH solution and extracted with EtOAc (×2). All organic phases were combined and washed with further 2M NaOH solution, dried and concentrated to give the title compound as an orange gum (1 g). δH (DMSO-d6, 400 MHz) 6.86 (1H, dd), 6.33 (1H, dd), 6.03 (1H, m), 5.32 (1H, d), 3.74 (3H, s), 3.33 (1H, br s), 3.18 (1H, m), 2.92 (2H, m), 2.51 (2H, m), 1.83 (2H, m), 1.17 (2H, m). MS (ES): MH+ 225.

Aufarbeitung

  1. stirringstirred for 2 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between EtOAc and saturated aqueous NaHCO3 solution
  4. washThe organic phase was washed with further saturated aqueous NaHCO3 solution
  5. concentrationThe aqueous was concentrated to ˜50% volume
  6. extractionextracted with EtOAc (×2)
  7. washwashed with further 2M NaOH solution
  8. customdried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8c366d2f332843359442afffe2adc62c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236953B2

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