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

HRID 2399430Notes

Reaction equation

HRID 2399430 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 stirred at room temperature under an argon atmosphere for 18 h. The mixture was partitioned between 1 N 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% ethylacetate/hexanes, provided a white solid (0.45 g, 82%): m.p. 55°-57° C.

Workup

  1. customThe mixture was partitioned between 1 N 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% ethylacetate/hexanes

Sources & evidence

ORD record
ord-ebf36099290141bcb8c1ca3344b9c64e
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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