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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 278999Generated: October 27, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

https://huagongshe.com/reaction/278999

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dioneHCID 22624038—
SolventPiperidineHCID 8082—
Product2-Benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 22624063—

Reaction Steps

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.1 mmol, from Example M) was reacted in piperidine (3.0 mL) in the presence of DBU (0.05 mL) following the procedure of Example 18 to give 0.8 g of 2-benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione. Hydrogenation of 2-benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.4 g, 1.0 mmol) in the presence of 10% Pd/C (0.2 g) in DMA (30 mL) afforded 0.28 g of the title compound, mp 222-224° C.;

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06362181B1
Source datasetuspto-grants-2002_03
ORD IDord-d3201f4748654f1eaeae47c0a2b36baf
Source noteuspto-grants-2002_03