3-Iodothiophene → Butyl 4-(3-thienyl)piperazine-1-carboxylate

HRID 390323

반응식

HRID 390323 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])(C)C)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.I[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1.[CH3:20][C:21](C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.O>[S:17]1[CH:18]=[CH:19][C:15]([N:4]2[CH2:3][CH2:2][N:1]([C:7]([O:9][CH2:10][CH2:13][CH2:20][CH3:21])=[O:8])[CH2:6][CH2:5]2)=[CH:16]1

참가 물질

7

반응물 4

HCID 663323-IodothiopheneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxide

생성물 1

HCID 86672487Butyl 4-(3-thienyl)piperazine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of tert-butyl piperazine-1-carboxylate (0.300 g, 1.61 mmol) in 10 mL of toluene under an atmosphere of nitrogen was added 3-iodothiophene (0.390 g, 1.86 mmol), sodium tert-butoxide (0.310 g, 3.22 mmol), tris (dibenzylidenacetone)palladium (0) (0.295 g, 0.322 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos, 0.307 g, 0.644 mmol). The mixture was heated to 100° C. for 18 h, cooled to rt, and treated with water. The solution was extracted 3× with ethyl acetate, and the combined organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography, eluting with 0-70% ethyl acetate, to provide text-butyl 4-(3-thienyl)piperazine-1-carboxylate that gave a proton NMR spectra consistent with theory.

후처리

  1. temperaturecooled to rt
  2. extractionThe solution was extracted 3× with ethyl acetate
  3. washthe combined organic solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified via silica gel chromatography
  8. washeluting with 0-70% ethyl acetate

출처 및 근거

ORD 기록
ord-614555e96b724d83b2a7fb7b81e7bf0b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383638B2

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