Acetic Acid → HCID 69584053, compound

HRID 988180Notes

Reaction equation

HRID 988180 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)[CH2:3][CH2:2]1.[CH:17]([C:19]1[NH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:27]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=O.N1CCCC1.C(O)(=O)C>C(O)C>[O:16]=[C:10]1[C:9](=[CH:17][C:19]2[NH:20][C:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=3[C:27]=2[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH:4]2[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]2)[NH:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acidHCID 221353964-(Piperidin-4-yl)indolin-2-one

Product 1

HCID 69584053HCID 69584053, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (45 mg, 0.2 mmol), 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (57 mg, 0.23 mmol) and pyrrolidine (0.3 mL) in ethanol (0.5 mL) was heated to reflux for 2 hours. Acetic acid (0.05 mL) was added to the reaction and heating was continued for another 10 minutes. The reaction was cooled and the precipitate which formed was collected by vacuum filtration, washed with ethanol and dried to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureheating
  4. temperatureThe reaction was cooled
  5. customthe precipitate which formed
  6. filtrationwas collected by vacuum filtration
  7. washwashed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-312db2c8a6d349818b2bc504d560d8dc
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

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