Potassium Carbonate → Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate

HRID 16823

반응식

HRID 16823 반응식
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:13]1([N:17]2[CH2:22][CH2:21][N:20]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 47386021-Cyclobutylpiperazine

생성물 1

HCID 57440408Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate수율 33%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

Ethyl 4-fluorobenzoate (0.753 g, 4.48 mmol) was added to a solution of 1-cyclobutylpiperazine (0.571 g, 4.07 mmol) and potassium carbonate (0.563 g, 4.07 mmol) in DMSO (8 mL) under nitrogen. The resulting solution was stirred at 100° C. for 18 h and evaporated to dryness. The residue was triturated with diethyl ether, filtered, and evaporated and the crude product was purified by silica column chromatography, eluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate (0.387 g, 32.9%) as a white solid.

후처리

  1. customevaporated to dryness
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. customevaporated
  5. customthe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 2.5% 2.5N MeOH in DCM
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-4a50fabbb59a43498f3a1e1ac535a4bc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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