Hydroxylamine HCl → HCID 73444589, compound

HRID 1790447Notes

Reaction equation

HRID 1790447 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=O)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[OH:28][NH3+:29].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[N:29][OH:28])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 220380721-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindoline

Product 1

HCID 73444589HCID 73444589, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of crude 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-formylindoline (35 g), hydroxylammonium chloride (10.4 g) and anhydrous sodium acetate (12.3 g) in ethanol (400 ml) was stirred at room temperature for a day. Then the reaction solution was concentrated under reduced pressure, diluted with ethyl acetate (500 ml), an 8 N aqueous solution (30 ml) of sodium hydroxide and water (100 ml) and the layers were separated. The organic layer was washed with brine and dried over magnesium sulfate. After removing the solvent, the residue was dissolved in a hot toluene (100 ml)-isopropyl ether (100 ml) mixtures and allowed to cool at room temperature. The resulting crystals were collected by filtration and dried at 50° C. to give the title compound (31 g) as a pale yellow powder (yield: 85%).

Workup

  1. concentrationThen the reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate (500 ml)
  3. customan 8 N aqueous solution (30 ml) of sodium hydroxide and water (100 ml) and the layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removing the solvent
  7. dissolutionthe residue was dissolved in a hot toluene (100 ml)-isopropyl ether (100 ml) mixtures
  8. temperatureto cool at room temperature
  9. filtrationThe resulting crystals were collected by filtration
  10. customdried at 50° C.

Sources & evidence

ORD record
ord-bac566a5a11f4e82b6bb453578a6c236
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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