4-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine → 2-Methoxy-4-(1-propylpiperidin-4-yl)aniline

HRID 419475노트

반응식

HRID 419475 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCOC(C)=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

참가 물질

3

반응물 1

HCID 598602684-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

생성물 1

HCID 598602732-Methoxy-4-(1-propylpiperidin-4-yl)aniline수율 80.2%

시약·촉매·용매 1

HCID 21584119Ethylacetate methanol용매

실험 절차

4-[3-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (3.33 g, 12.05 mmol) was placed in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/C (4.7 g, 1.2 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (50 psi). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to give the title compound of step D (2.4 g, 9.66 mmol, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 6.68 (s, 1H), 6.63 (s, 2H), 3.81 (s, 3H), 3.52 (bs, 2H), 3.07 (d, J=11.90 Hz, 2H), 2.40 (s, 1H), 2.32-2.38 (m, 2H), 1.98-2.07 (m, 2H), 1.80 (ddd, J=12.32, 6.00, 3.30 Hz, 4H), 1.51-1.61 (m, 2H), 0.91 (t, J=7.42 Hz, 3H).

후처리

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe next morning the vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

출처 및 근거

ORD 기록
ord-f29c5c4ced3c4d82b1c1fb24a1c7cd40
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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