Piperidine → HCID 66675422, compound

HRID 1008251Notes

Reaction equation

HRID 1008251 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.N1CCCCC1>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:17]/[C:13]3[NH:12][CH:16]=[CH:15][CH:14]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 13854Pyrrole-2-carboxaldehydeHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 66675422HCID 66675422, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-bromo-1,3-dihydro-2H-indol-2-one (100 mg, 0.47 mmol), 1H-pyrrole-2-carbaldehyde (49.2 mg, 0.52 mmol), and piperidine (0.02 mL, 0.2 mmol) in methanol (3 mL) was stirred at 65° C. for 2 hours, cooled to room temperature, and filtered. The filter cake was washed with hexanes to provide the desired product (65 mg, 48%). MS (DCI/NH3) m/z 290 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with hexanes

Sources & evidence

ORD record
ord-7f09e85bbaa241508aecacb30fb32c31
Source dataset
uspto-grants-2004_09
Patent number
US06797825B2

Reaction notes

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