3-Methylpiperidine → 2-Benzyloxy-5-bromo-6-(3-methyl-piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278965Notes

Reaction equation

HRID 278965 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:26])[C:22]([N+:23]([O-])=O)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][CH:29]1[CH2:34][CH2:33][CH2:32]N[CH2:30]1>CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:26])[C:22]([N:23]3[CH2:32][CH2:33][CH2:34][CH:29]([CH3:30])[CH2:28]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 790813-MethylpiperidineHCID 226239822-Benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239512-Benzyloxy-5-bromo-6-(3-methyl-piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione (0.50 g, 1.2 mmol, from Example S1-A) in DMF (5 mL) was added 3-methylpiperidine (0.47 g, 4.7 mmol). The reaction was reacted at 120° C. for 5 hours, cooled, and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel using hexane/ethyl acetate (5:1) to give 0.50 g of the title compound.

Workup

  1. customThe reaction was reacted at 120° C. for 5 hours
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1375ce456f464164a2eb7c73ed686286
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

Loading…