Reaktion #1561573

Reaktionsgleichung

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

DIEA

AcOH

NaCNBH3

5-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde

→

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

Lösungsmittel

DCM MeOH

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction solution was stirred at ambient temperature overnight
2. 2
   Extraktionextracted with DCM
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified with prep-TLC

Vorschrift

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.

Quelle