Triphenylphosphine → 2-[1-(4-Pyridyl)piperidin-4-ylmethoxy]aniline

HRID 346673

Reaktionsgleichung

Reaktionsgleichung von HRID 346673
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(OC([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][O:14][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH2:22])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4935485N-Boc-2-aminophenolHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanol

Produkt 1

HCID 210802922-[1-(4-Pyridyl)piperidin-4-ylmethoxy]anilineAusbeute 236,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-pyridyl)piperidin-4-ylmethanol (357 mg) and 2-tert-butyloxycarbonylaminophenol (328 mg) in tetrahydrofuran (15 ml) was added triphenylphosphine (447 mg) followed by diethyl azodicarboxylate (0.27 ml). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated to a gum which was purified by column chromatography on silica eluting with methanol/dichloromethane (10:90) to give the tert-butyloxycarbonyl protected derivative of 2-[1-(4-pyridyl)piperidin-4-ylmethoxy]aniline (1.05 g);

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to a gum which
  2. customwas purified by column chromatography on silica eluting with methanol/dichloromethane (10:90)

Quellen und Nachweise

ORD-Eintrag
ord-d422d900877642118b1fc47c2f655ce1
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173025B1

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