Water → t-Butyl 4-[4-(5-nitropyridin-2-yloxy)benzyl]piperazine-1-carboxylate

HRID 884149Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[N:26]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.O>CN(C=O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:17]=[CH:18][C:3]([CH2:2][N:29]3[CH2:28][CH2:27][N:26]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30]3)=[CH:4][CH:5]=2)=[N:9][CH:10]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(4-chloromethylphenoxy)-5-nitropyridine (12.32 g, 47 mmol) in DMF (120 mL) were added triethylamine (19.4 mL, 140 mmol) and t-butyl piperazine-1-carboxylate 11.27 g, 61 mmol), and the resulting solution was stirred for 3 hours at 50° C. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby yield 11.26 g of the title compound.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water and brine
dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
customevaporated
customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-498ce6d889154815b55ad8fdd5e1a1fb
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236826B2

Reaction notes

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