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

HRID 1014194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014194
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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b33ef526b01d4d2686d331f438668f1b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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