Hydroxyamine hydrochloride → 4-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl]cyclohexan-1-one oxime

HRID 1780857Notes

Reaction equation

HRID 1780857 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:12]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:32][OH:33]>N1C=CC=CC=1>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:12]([O:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:11]=2)[CH2:4][CH2:5][C:6](=[N:32][OH:33])[CH2:7][CH2:8]1)#[N:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 152952054-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl)cyclohexan-1-one

Product 1

HCID 189736834-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl]cyclohexan-1-one oximeYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl)cyclohexan-1-one (0.525 g, 1.49 mmol) and hydroxylamine hydrochloride (0.114 g, 1.63 mmol) in pyridine (5 mL) was was stirred at room temperature under an argon atmosphere for 18 h. The mixture was partitioned between 1N hydrochloric acid and methylene chloride, the organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 35% ethyl acetate/hexanes, provided a white solid (0.45 g, 82%): m.p. 55°-57° C.

Workup

  1. customThe mixture was partitioned between 1N hydrochloric acid and methylene chloride
  2. extractionthe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customPurification by flash chromatography
  6. washeluting with 35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1b082d2f9b9442db8c8b65da20b61200
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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