Hydroxyamine hydrochloride → HCID 76568486, compound

HRID 2382987Notes

Reaction equation

HRID 2382987 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=O)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>CCO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[N:24][OH:25])[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57567390HCID 57567390, compound

Product 1

HCID 76568486HCID 76568486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1′-benzylspiro[indene-1,4′-piperidin]-3(2H)-one lab (38 g, 0.15 mol) in EtOH (300 mL), hydroxylamine hydrochloride (18 g, 0.30 mol) and sodium acetate (19.5 g, 0.275 mol) were added. The mixture was refluxed for 4 hours and the solvent removed under reduced pressure. The residue was diluted with 150 mL water and 100 mL CH2Cl2. After the mixture was stirred for 10 min, the resulting white solid was collected by filtration. The organic phase in the filtrate was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. After evaporation of the solvent under reduced pressure, a yellow oil was obtained. The oil was crystallized from EtOAc to yield 1′-benzylspiro[indene-1,4′-piperidin]-3(2H)-one oxime 1ac as an off-white solid. 1H NMR (CD3OD, 400 MHz) δ 7.64 (d, J=8.0 Hz, 1H), 7.55-7.57 (m, 2H), 7.38-7.50 (m, 5H), 7.29-7.33 (m, 1H), 4.25 (s, 2H), 3.41 (d, J=12.4 Hz, 2H), 3.08 (t, J=12.0 Hz, 2H), 2.95 (s, 2H), 2.20-2.28 (m, 2H), 1.68 (d, J=14.4 Hz, 2H).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customthe solvent removed under reduced pressure
  3. additionThe residue was diluted with 150 mL water and 100 mL CH2Cl2
  4. filtrationthe resulting white solid was collected by filtration
  5. customThe organic phase in the filtrate was separated
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. customAfter evaporation of the solvent under reduced pressure
  10. customa yellow oil was obtained
  11. customThe oil was crystallized from EtOAc

Sources & evidence

ORD record
ord-f4f964d531e64e8286a6121e16a465d5
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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