Acetic Acid → 1,4-bis[(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine

HRID 1474391노트

반응식

HRID 1474391 반응식
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[CH2:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.CC(O)=O.[BH3-]C#N.[Na+].[Br:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH2:39][CH2:40][O:41][CH:42]2[CH:47]=O>C(Cl)Cl.CO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:47][CH:42]2[C:43]3[C:38](=[C:37]([Br:36])[CH:46]=[CH:45][CH:44]=3)[CH2:39][CH2:40][O:41]2)[CH2:17][CH2:18]1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 666439161-[(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazineHCID 772312485-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde

생성물 1

HCID 684302901,4-bis[(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine

시약·촉매·용매 2

HCID 962Water용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 1-[(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine (160 mg, 0.52 mmol) in DCM/MeOH (1:1, 5 mL) was added DIEA (134 mg, 1.03 mmol), and then mixture was stirred at r.t for 10 min. Then AcOH (62 mg, 1.03 mmol), NaCNBH3 (65 mg, 1.03 mmol) and 5-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde (125 mg, 0.516 mmol) were added into the mixture. The reaction solution was stirred at ambient temperature overnight. The reaction mixture was added water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to give the product 1,4-bis[(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine.

후처리

  1. stirringThe reaction solution was stirred at ambient temperature overnight
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with prep-TLC

출처 및 근거

ORD 기록
ord-5547f1cf9b864cfb9ccfdedac0e77816
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018211B2

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