Hydroxyamine hydrochloride → HCID 86594056, compound

HRID 1179083Notes

Reaction equation

HRID 1179083 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[NH2:18][OH:19]>C(O)C>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[N:18][OH:19])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 86594056HCID 86594056, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Dimethylamino-4-phenylcyclohexanone (10 g) and hydroxylamine hydrochloride (4.8 g) were dissolved in absolute ethanol (120 ml), basic ion exchanger Amberlyst A 21 (30.7 g) was added to the solution, and stirring was carried out overnight at RT. The ion exchanger was filtered off and washed with ethanol (3×50 ml) on the frit. The ethanol was removed in vacuo and the residue was adjusted to pH 11 with 5M NaOH, diluted with water and extracted with ethyl acetate (4×30 ml). The combined extracts were dried with Na2SO4 and concentrated. 11 g of 4-dimethylamino-4-phenyl-cyclohexanone oxime were obtained.

Workup

  1. filtrationThe ion exchanger was filtered off
  2. washwashed with ethanol (3×50 ml) on the frit
  3. customThe ethanol was removed in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate (4×30 ml)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ffbaeabb60e0437599a755b70f6272d5
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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