Ethanolamine → HCID 21071615, compound

HRID 1666821Notes

Reaction equation

HRID 1666821 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 0.1 N 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 0.1 N 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-06afa83982ae4b2c8411e6c69842a6a4
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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