Hydroxyamine hydrochloride → HCID 73508909, compound

HRID 2253697Notes

Reaction equation

HRID 2253697 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5](=O)[CH:4]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:3]1.Cl.[NH2:23][OH:24]>N1C=CC=CC=1>[O:1]=[C:2]1[CH2:7][CH2:6][C:5](=[N:23][OH:24])[CH:4]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:3]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19012931HCID 19012931, compound

Product 1

HCID 73508909HCID 73508909, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2,5-dioxo-6-benzhydrylpiperidine (15.35 gm, 55 mmole) in pyridine (150 ml) was added hydroxylamine hydrochloride (10.63 gm, 165 mmole) and the reaction mixture was stirred for 15 min. The reaction mixture was concentrated under vacuum, and the contents were poured into 1N HCl (250 ml). The aqueous phase was extracted with methylene chloride (2×300 ml) and dried (anhyd. magnesium sulfate). The methylene chloride was removed under vacuum to afford 2-oxo-5-oximino-6-benzhydrylpiperidine (10.62 gms, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe contents were poured into 1N HCl (250 ml)
  3. extractionThe aqueous phase was extracted with methylene chloride (2×300 ml)
  4. dry with materialdried (anhyd. magnesium sulfate)
  5. customThe methylene chloride was removed under vacuum

Sources & evidence

ORD record
ord-8522256eed0546f2b194f7d2d8150dd1
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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