Hydroxyamine hydrochloride → 4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one oxime

HRID 1780844Notes

Reaction equation

HRID 1780844 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=[N:25][OH:26])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 9861604SB-200473

Product 1

HCID 189737034-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one oximeYield 95.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.125 g, 0.4 mmol) in pyridine (2 mL) was added hydroxylamine hydrochloride (0.031 g, 0.44 mmol), the mixture was stirred at room temperature under an argon atmosphere for 4 h and the solvent was evaporated. The mixture was partitioned between water and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/hexanes, followed by trituration of the product with ether/hexanes provided a white solid (0.125 g, 95%): m.p. 50°-53° C. Analysis Calc. for C19H24N2O3 : C 69.44, H 7.37, N 8.53; found: C 69.35, H 7.47, N 8.28.

Workup

  1. customthe solvent was evaporated
  2. customThe mixture was partitioned between water and ethyl acetate
  3. extractionwas extracted twice with ethyl acetate
  4. extractionthe organic extract
  5. dry with materialwas dried (potassium carbonate)
  6. customthe solvent was removed in vacuo
  7. customPurification by flash chromatography
  8. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-72c306df65b04b39bdd396e4a5d04fb1
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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