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

HRID 16823

反応式

HRID 16823 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a50fabbb59a43498f3a1e1ac535a4bc
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

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