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

HRID 883767노트

반응식

HRID 883767 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 57699516N-[4-Fluoro-3-(methyloxy)phenyl]-4-piperidinamine수율 99.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c366d2f332843359442afffe2adc62c
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236953B2

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