4-(3-Methoxy-4-nitrophenyl)pyridine → 2-(Methyloxy)-4-(4-piperidinyl)aniline

HRID 419558노트

반응식

HRID 419558 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CC(O)=O.CC(O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

참가 물질

5

반응물 1

HCID 137288334-(3-Methoxy-4-nitrophenyl)pyridine

생성물 1

HCID 594529072-(Methyloxy)-4-(4-piperidinyl)aniline수율 12%

시약·촉매·용매 3

HCID 82844Platinum oxide (PtO)촉매HCID 176Acetic Acid용매HCID 3776Isopropanol용매2회

실험 절차

To 4-[3-(methyloxy)-4-nitrophenyl]pyridine (Example 137, step A) (4.6 g, 20 mmol) in HOAc (20 mL) is added platinum oxide (460 mg, 2 mmol). The reaction was evacuated then refilled with 60 psi H2 gas. The reaction was stirred under a H2 atmosphere for 3 days. The reaction was evacuated and the atmosphere replaced with N2. The solvent was removed under vacuum, and the residue taken up in DCM/MeOH. Silica was added, and the solvent removed under vacuum. Silica gel chromatography provided material which contained product and other impurities. This material was dissolved in iPrOH and allowed to stand overnight. The crystals which formed were collected by decanting off the solvent and rinsing with iPrOH. Obtained the title compound of step A (500 mg, 2.4 mmol, 12%) slightly wet with iPrOH as colorless crystals. 1H NMR (400 MHz, DMSO-d6) δ 6.68-6.60 (m, 3H), 3.83 (s, 3H), 3.71 (br s, 2H), 3.38-3.31 (m, 2H), 2.85-2.75 (m, 2H), 2.59-2.49 (m, 1H), 1.91-1.75 (m, 5H).

후처리

  1. customThe reaction was evacuated
  2. additionthen refilled with 60 psi H2 gas
  3. customThe reaction was evacuated
  4. customThe solvent was removed under vacuum
  5. additionSilica was added
  6. customthe solvent removed under vacuum
  7. customSilica gel chromatography provided material which
  8. waitto stand overnight
  9. customThe crystals which formed
  10. customwere collected
  11. customby decanting off the solvent
  12. washrinsing with iPrOH

출처 및 근거

ORD 기록
ord-95dc5de5cae743668b3eb387e017d351
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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