Hydroxyamine hydrochloride → 4-Dimethylamino-1-methyl-4-phenyl-cyclohexane carbaldehyde oxime

HRID 1477210Notes

Reaction equation

HRID 1477210 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][C:6]([CH3:11])([CH:9]=O)[CH2:5][CH2:4]1.Cl.[NH2:20][OH:21]>C(O)C>[CH3:1][N:2]([CH3:18])[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][C:6]([CH3:11])([CH:9]=[N:20][OH:21])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866346824-Dimethylamino-1-methyl-4-phenyl-cyclohexane carbaldehyde

Product 1

HCID 875238174-Dimethylamino-1-methyl-4-phenyl-cyclohexane carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the title compound of step 2 (5.90 g, 24.0 mmol) and hydroxylamine hydrochloride (2.50 mg, 36.0 mmol) in abs. ethanol (100 mL) were mixed with Amberlyst A 21 (17.0 g) and stirred for 20 h at RT. The ion exchanger was filtered off, the solution concentrated to low volume and the residue made alkaline with 1N NaOH. The aqueous phase was extracted with ethyl acetate, dried over Na2SO4 and concentrated to low volume in a vacuum.

Workup

  1. filtrationThe ion exchanger was filtered off
  2. concentrationthe solution concentrated to low volume
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-cf3794f8be844bfd9e09a54a4e9011a7
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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