2-Bromobenzoic acid → Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate

HRID 1665584노트

반응식

HRID 1665584 반응식
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43]>CN(C=O)C.O>[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][N:52]([C:23](=[O:25])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[Br:20])[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:43])[CH3:44]

참가 물질

8

반응물 5

HCID 69402-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 17952334Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate수율 90.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
10 °C

실험 절차

HOBt (4 g, 29.6 mmol) and DIEA (8.7 g, 67.7 mmol) were added to a stirred solution of 2-bromo benzoic acid (5.6 g, 28.3 mmol) in DMF (50 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (7.76 g, 40.48 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (5 g, 26.9 mmol) were added. Then reaction mixture was stirred at the room temperature overnight. Water was added and the product was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4, and removed under reduced pressure to afford 9 g (90%) of 4-(2-bromo-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. 1H NMR: (DMSO-d6): δ 7.58 (d, 1H), 7.38 (t, 1H), 7.29 (d, 1H), 7.24 (d, 1H), 3.85 (m, 1H), 3.7 (m, 1H), 3.55 (t, 2H), 3.5 (m, 1H), 3.3 (m, 3H), 3.15 (m, 1H), 1.45 (s, 9H).

후처리

  1. additionwere added
  2. customThen reaction mixture
  3. extractionthe product was extracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. customremoved under reduced pressure

출처 및 근거

ORD 기록
ord-334e494e16b343ddb98163ad28039856
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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