N-Boc-3-[(1-Cbz-4-piperidyl)oxy]aniline → 1-Cbz-4-(3-aminophenoxy)-piperidine

HRID 499191Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24]C(OC(C)(C)C)=O)[CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 22 °C

Procedure

4-(3-tert-Butoxycarbonylamino-phenoxy)-piperidine-1-carboxylic acid benzyl ester (11.8 g, 27.6 mmol) is dissolved in a solution of trifluoroacetic acid in dichloromethane (25% v/v, 20 mL). The reaction mixture is stirred at 22° C. for 60 min. After removal of the solvent, the oily residue is dissolved in dichloromethane (250 mL) and neutralized with 0.2 N aqueous sodium hydroxide solution (250 mL) and extracted with dichloromethane (10×100 mL) followed by ethyl acetate (5×100 mL). The combined organic phases are dried over anhydrous sodium sulfate. After removal of solvent, the crude product is purified on silica gel chromatography with dichloromethane-methanol to give a light brown oil (4.84 g, 54%, ES+(m/z) 327.3 [M+H]).

Workup

customAfter removal of the solvent
dissolutionthe oily residue is dissolved in dichloromethane (250 mL)
extractionextracted with dichloromethane (10×100 mL)
dry with materialThe combined organic phases are dried over anhydrous sodium sulfate
customAfter removal of solvent
customthe crude product is purified on silica gel chromatography with dichloromethane-methanol
customto give a light brown oil (4.84 g, 54%, ES+(m/z) 327.3 [M+H])

Sources & evidence

ORD record: ord-1423ec6a4ad149ad98a04e0a774cde5c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767674B2

Reaction notes

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