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Water → HCID 59204950, compound

HRID 2241909
Notes
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Reaction equation

HRID 2241909 reaction equation
O.NN.[F:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][N:22]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:16][CH2:15]1.O>C(O)C>[F:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][NH2:22])[CH2:18][CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 592050452-{2-[1-(2-Fluoro-4-nitrophenyl)piperidin-4-yl]ethyl}isoindoline-1,3-dione

Product 1

HCID 59204950HCID 59204950, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydrazine monohydrate (0.272 ml, 5.61 mmol) was added to a solution of 2-{2-[1-(2-fluoro-4-nitrophenyl)piperidin-4-yl]ethyl}isoindoline-1,3-dione (compound of Reference Example 66; 0.745 g, 1.87 mmol) in ethanol (5 ml), and the mixture was stirred at 80° C. for 1 hour. Water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.170 g, 34%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7e0459b2c53434985fa17b7cbfde484
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07671058B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes