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Ethyl Acetate → 1-Benzyl-4-(cyclopropylcarbonyl)piperazine

HRID 1972724
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인쇄 미리보기

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HRID 1972724 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>ClCCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:17]([CH:14]2[CH2:16][CH2:15]2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 759941-BenzylpiperazineHCID 77637Cyclopropanecarbonyl chlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 12200501-Benzyl-4-(cyclopropylcarbonyl)piperazine수율 99.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
50 °C

실험 절차

To a mixture of 1-benzyl-piperazine (1.20 g, 6.81 mmol) in anhydrous DCE (23 mL) was added cyclopropane carboxylic acid chloride (854 mg, 8.17 mmol, 1.2 eq) followed by diisopropylethylamine (1.3 mL, 7.49 mmol, 1.1 eq), and the reaction mixture was stirred at 50° C. under N2 for 15 h. The mixture was cooled to rt and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (Biotage®, gradient elution 75% EtOAc/hexane) to give the product (1.65 g, 99%) as a brown oil. 1H-NMR (300 MHz, DMSO-d6) 7.34 to 7.23 (m, 5H), 3.64 (broad s, 2H), 3.48 (s, 2H), 3.44 (broad s, 2H), 2.37 (broad s, 2H), 2.28 (broad s, 2H), 1.95 to 1.91 (m, 1H), 0.70 to 0.65 (m, 4H); ES-MS m/z 245.2 [M+H]+, RT (min) 1.12.

후처리

  1. temperatureThe mixture was cooled to rt
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MPLC (Biotage®, gradient elution 75% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-19e3b755b5bd4cd1aad2faf76f900693
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431695B2

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