Trifluoroacetic acid → 1-[3-(Methyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine

HRID 419394노트

반응식

HRID 419394 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 594526201,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate

생성물 1

HCID 594529341-[3-(Methyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1,1-dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate (5.67 g, 13.5 mmol) and DCM (110 mL) was cooled with an ice/H2O bath. TFA (30.0 mL, 389 mmol) was added dropwise via addition funnel. Upon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL), extracted with DCM, dried (MgSO4) and concentrated to provide the title compound of step D (4.01 g, 12.5 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.31 (m, 2H), 1.68 (d, J=9.9 Hz, 2H), 2.22-2.32 (m, 2H), 2.34-2.45 (m, 2H), 2.54-2.61 (m, 4H), 2.95 (d, J=12.1 Hz, 2H), 3.36-3.43 (m, 4H), 3.88 (s, 3H), 6.50 (d, J=2.6 Hz, 1H), 6.57 (dd, J=9.4, 2.4 Hz, 1H), 7.86 (d, J=9.5 Hz, 1H).

후처리

  1. customUpon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL)
  2. extractionextracted with DCM
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-170112aed4384c3cb920dde85df108f1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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