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

HRID 1187134ノート

反応式

HRID 1187134 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c43763d2ad854fdda8799a5744ac4c22
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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