1-Benzylpiperazine → 1-[2-(2-Oxazolyl)phenyl]-4-(phenylmethyl)piperazine

HRID 2294111Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[O:27][CH:28]=[CH:29][N:30]=1>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[O:27][CH:28]=[CH:29][N:30]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-benzylpiperazine (3.56 g, 20.2 mmol) in 25 mL of THF was cooled to 0° C. and then n-butyllithium was added. The mixture was stirred at 0° C. for 30 minutes and at room temperature for an additional hour. The mixture was cooled to 0° C. and then 2-fluoro-1-oxazol-2-ylbenzene (1.1 g, 6.75 mmol) was slowly added. The mixture was allowed to warm to room temperature and stirred at room temperature for 90 minutes. The mixture was quenched with water and the aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine, dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (10:1) to give 4-benzyl-1-(2-oxazol-2-ylphenyl)piperazine (0.805 g, 2.52 mmol).

Workup

temperatureThe mixture was cooled to 0° C.
temperatureto warm to room temperature
stirringstirred at room temperature for 90 minutes
customThe mixture was quenched with water
customthe aqueous layer was separated
extractionextracted with ethyl acetate (3×30 mL)
extractionThe combined extract
washwas washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified on silica gel by column chromatography
washeluting with hexanes/ethyl acetate (10:1)

Sources & evidence

ORD record: ord-8558ed40bfb04284812fdd36fb539722
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688795

Reaction notes

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