Ethanolamine → HCID 21071615, compound

HRID 1371879Notes

Reaction equation

HRID 1371879 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2C(=CC=CC=2)C1=O.C(CN)[OH:25].[OH2:28].[OH-:29].[Na+]>C1COCC1>[C:21]([OH:22])(=[O:25])[C:20]([OH:29])=[O:28].[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 14798Sodium HydroxideHCID 21071407HCID 21071407, compound

Product 1

HCID 21071615HCID 21071615, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 2-(2-(7-fluoro-1H-indol-3-yl)ethyl)isoindole-1,3-dione in 25 mL of THF. Add ethanolamine (63.4 g, 62.65 mL, 1038 mmol, 100 eq.) with vigorous stirring and heat to 70° C. After 1.5 hours, cool to room temperature. After 18 hours, pour reaction mixture into of water (250 mL) containing of 5N NaOH (3 mL) and extract with Et2O (2×200 mL). Combine the organic layers and wash with 0.1N NaOH. Collect the organic layer, dry over MgSO4, filter, and remove the solvent in vacuo to give the title compound as a yellow oil.

Workup

  1. temperaturecool to room temperature
  2. waitAfter 18 hours
  3. additionpour
  4. extractionextract with Et2O (2×200 mL)
  5. washCombine the organic layers and wash with 0.1N NaOH
  6. customCollect the organic layer
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-53951abb4e1842b792e03b8806e1ec38
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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