Ethanol → HCID 21949207, compound

HRID 2376885Notes

Reaction equation

HRID 2376885 reaction equation
O.NN.[OH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][N:14]2[C:22](=[O:23])C3C(=CC=CC=3)C2=O)[CH2:7][CH2:6]1.[CH2:25]([OH:27])[CH3:26]>>[OH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][NH:14][C:22](=[O:23])[O:27][CH2:25][C:26]2[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 21949315HCID 21949315, compound

Product 1

HCID 21949207HCID 21949207, compound

Procedure

Ethanol (100 ml) and hydrazine hydrate (1.5 g) were added to 2-(3-(4-hydroxypiperidino)propyl)isoindolin-1,3-dione (4.5 g); the reaction mixture was heated to reflux for 2.5 hours; and the produced crystals were filtered off. N-Methylmorpholine (2.5 ml) and N-(benzyloxycarbonyloxy)succinimide (5.2 g) were added to the filtrate; and the reaction mixture was stirred at room temperature overnight. Aqueous solution of sodium hydrogencarbonate was added to the reaction mixture; extraction was performed with ethyl acetate; and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to yield the title compound (2.96 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationand the produced crystals were filtered off
  4. additionN-Methylmorpholine (2.5 ml) and N-(benzyloxycarbonyloxy)succinimide (5.2 g) were added to the filtrate
  5. additionAqueous solution of sodium hydrogencarbonate was added to the reaction mixture
  6. extractionextraction
  7. washand the organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b606c974a58464c9dcce3df75a70d83
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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