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

HRID 1187134Notes

Reaction equation

HRID 1187134 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c43763d2ad854fdda8799a5744ac4c22
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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