Piperidine → HCID 178517066, compound

HRID 1615217Notes

Reaction equation

HRID 1615217 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[NH:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20]=O)=[CH:19][C:14]=2[N:13]=[N:12]1.N1CCCCC1>CCO>[NH:11]1[C:15]2[CH:16]=[CH:17][C:18](/[CH:20]=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 178519382HCID 178519382, compound

Product 1

HCID 178517066HCID 178517066, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A scintillation vial was charged with indolin-2-one (101 mg, 0.760 mmol), 1H-benzo[d][1,2,3]triazole-5-carbaldehyde (123 mg, 0.836 mmol), piperidine (7.5 uL, 0.076 mmol) and EtOH (4 mL). The reaction was then heated to 90° C. for 2 hrs. A yellow precipitate formed which was further precipitated by cooling to room temperature and adding more EtOH (5 mL). The yellow solid was then filtered and washed with EtOH (20 mL) giving 149 mg, 75% of the title compound. 1H NMR (400 MHz, d6-DMSO) δ 15.94 (s, 1H), 10.65 (s, 1H), 8.27 (bs, 1H), 8.05 (bs, 1H), 7.80 (s, 1H), 7.77 (bs, 1H), 7.51 (d, J=7.6 Hz, 1H), 7.24 (t, J=7.6 Hz, 1H), 6.88 (d, J=7.6 Hz, 1H), 6.84 (d, J=7.6 Hz, 1H); MS ESI 263.0 [M+H]+, calcd for [C15H10N4O+H]+ 263.09.

Workup

  1. customA yellow precipitate formed which
  2. customwas further precipitated
  3. temperatureby cooling to room temperature
  4. additionadding more EtOH (5 mL)
  5. filtrationThe yellow solid was then filtered
  6. washwashed with EtOH (20 mL)

Sources & evidence

ORD record
ord-21ee10a1847445559f596fd746238ba6
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…