Piperidine → HCID 59299849, compound

HRID 2236613Notes

Reaction equation

HRID 2236613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]2.[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([Br:24])[C:22]=1[OH:23])[CH:18]=O.N1CCCCC1>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:18]\[C:17]1[CH:16]=[C:15]([Br:14])[C:22]([OH:23])=[C:21]([Br:24])[CH:20]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 120233176-Bromoisoquinoline-1,3-diol

Product 1

HCID 59299849HCID 59299849, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

6-Bromo-4H-isoquinoline-1,3-dione (0.12 g, 0.5 mmol), 3,5-dibromo-4-hydroxybenzaldehyde (0.14 g, 0.5 mmol), and piperidine (0.075 mL, 0.75 mmol) were dissolved in i-propanol (2 mL). After heating at 95° C. for 3 h, it is cooled, and the solid is filtered and washed with I-propanol, ether and hexane to yield 0.25 g (99.6%) solid; mp 167-168° C.; HRMS (ESI) m/z 499.8 (M−H)−1.

Workup

  1. temperatureit is cooled
  2. filtrationthe solid is filtered
  3. washwashed with I-propanol, ether and hexane

Sources & evidence

ORD record
ord-d679cc93899640568ec9c8a96369550d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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