Benzoic acid, 4-fluoro-, ethyl ester → Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate

HRID 16781

반응식

HRID 16781 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>CC(N(C)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

4

반응물 2

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

생성물 1

HCID 57440408Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate수율 11.31%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

Ethyl 4-fluorobenzoate (0.225 mL, 1.53 mmol) and 1-cyclobutylpiperazine (0.430 g, 3.07 mmol) were taken up in DMA (3 mL) and sealed into a microwave tube. The reaction was heated to 150° C. for 90 mins in the microwave reactor and cooled to room temperature. The reaction was not complete, so it was reheated at 150° C. for a further 1 h. The reaction mixture was evaporated to dryness and the crude product purified by silica column chromatography, eluting with a gradient of 0-2.5% MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate (0.050 g, 11.31%) as a yellow solid.

후처리

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was evaporated to dryness
  4. customthe crude product purified by silica column chromatography
  5. washeluting with a gradient of 0-2.5% MeOH in DCM
  6. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-6c3cf9423faf4786bc8b745bf2d949bb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

연결된 노트

불러오는 중…