Potassium Hydroxide → 1,1-Dimethylethyl 4-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1-piperazinecarboxylate

HRID 2251192Notes

Reaction equation

[OH-].[K+].Br[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([CH3:15])[O:12][N:11]=2)=[CH:6][CH:5]=1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([C:4]2[CH:9]=[CH:8][C:7]([C:10]3[N:14]=[C:13]([CH3:15])[O:12][N:11]=3)=[CH:6][CH:5]=2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A well stirred mixture of 0.015 mmol of bis(tri-t-butylphosphine)palladium, 0.01 mmol of cetyltrimethylammonium bromide, 2 mmol of powdered potassium hydroxide, 2 mmol of 3-(4-bromo-phenyl)-5-methyl-[1,2,4]oxadiazole and 2.1 mmol of N-BOC-piperazine in 1 ml of toluene was heated under Ar to 90° C. for 17 hours. The resulting reaction mixture was diluted with water, extracted with ethyl acetate and the product purified by column chromatography (SiO2; cyclohexane/ethyl acetate 7:3) to yield the title compound as a yellowish solid. MS (m/e): 345.3 (MH+, 100%)

Workup

customThe resulting reaction mixture
extractionextracted with ethyl acetate
customthe product purified by column chromatography (SiO2; cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record: ord-a60e94d179cc4581bd796294afbec794
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319099B2

Reaction notes

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