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

HRID 346673

Reaction equation

HRID 346673 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 210802922-[1-(4-Pyridyl)piperidin-4-ylmethoxy]anilineYield 236.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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);

Workup

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

Sources & evidence

ORD record
ord-d422d900877642118b1fc47c2f655ce1
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Linked notes

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