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

HRID 1932506Notes

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-c768ced0fb164bd78b416631432fbdaf
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188277B2

Reaction notes

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