Potassium Carbonate → 1-(4-Amino-3-methoxyphenyl)piperidin-4-ol

HRID 1014194노트

반응식

HRID 1014194 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)=[CH:3][C:4]=1[O:11][CH3:12]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 27792505-Fluoro-2-nitroanisole

생성물 1

HCID 573534601-(4-Amino-3-methoxyphenyl)piperidin-4-ol수율 63%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A solution of 4-fluoro-2-(methyloxy)-1-nitrobenzene (3.0 g, 17.5 mmol), 4-hydroxypiperidine (1.77 g, 17.5 mmol) and potassium carbonate (2.9 g, 21 mmol) in DMSO was stirred for 24 h. The reaction was diluted with water and extracted three times with Ethyl acetate. The combined organic solutions were dried over MgSO4 and concentrated. The resulting residue was stirred in ethanol and acetic acid with 10% Pd/C under 30 psi of hydrogen for 16 hr. The reaction was filtered through a pad of celite, rinsed with Ethyl acetate. The filtrate was concentrated and dissolved in methylene chloride. The organic solution was washed with saturated sodium bicarbonate, dried over MgSO4, and concentrated to give 1-[4-amino-3-(methyloxy)phenyl]-4-piperidinol (2.44 g, 63% yield over 2 steps). 1H NMR (400 MHz, d6-DMSO) δ 6.49-6.45 (m, 2H), 6.27 (dd, J=8.4 and 2.4 Hz, 1H), 4.60 (d, J=4.0 Hz, 1 H), 4.18 (s, 2H), 3.71 (s, 3H), 3.54-3.48 (m, 1H), 3.25-3.22 (m, 2H), 2.63-2.56 (M, 2H), 1.80-1.76 (m, 2H), 1.51-1.42 (m, 2H).

후처리

  1. extractionextracted three times with Ethyl acetate
  2. dry with materialThe combined organic solutions were dried over MgSO4
  3. concentrationconcentrated
  4. filtrationThe reaction was filtered through a pad of celite
  5. washrinsed with Ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. dissolutiondissolved in methylene chloride
  8. washThe organic solution was washed with saturated sodium bicarbonate
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b33ef526b01d4d2686d331f438668f1b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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