Water → Tert-butyl 4-(but-3-yn-1-yl)piperazine-1-carboxylate

HRID 1749950Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]#[CH:5].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:2]([N:16]1[CH2:15][CH2:14][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:18][CH2:17]1)[CH2:3][C:4]#[CH:5]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4-bromo-1-butyne (0.500 g, 3.76 mmol) in acetonitrile (20 mL) was added with 1-tert-butoxycarbonylpiperazine (0.700 g, 3.76 mmol) and potassium carbonate (0.779 g, 5.64 mmol), and the mixture was stirred at 60° C. for 6 hours. The reaction mixture was added with water, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-(but-3-ynyl)piperazine-1-carboxylate (0.621 g, 69%).

Workup

extractionthe mixture was extracted with methylene chloride
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-bc26f693f0114d59b966c26098f5faca
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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