Hydroxyamine hydrochloride → HCID 73993364, compound

HRID 1392146Notes

Reaction equation

HRID 1392146 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[S:7]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])=[O:8].Cl.[NH2:25][OH:26].C([O-])(=O)C.[K+]>CO>[OH:26][N:25]=[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[S:7]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 22719704HCID 22719704, compound

Product 1

HCID 73993364HCID 73993364, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(cyclohexanone-2-sulfonyl)-4-(4-fluorophenyl)piperazine (50 mg, 0.14 mmol), hydroxylamine hydrochloride (51 mg, 0.73 mmol) and potassium acetate (72 mg, 0.73 mmol) in methanol (5 ml) was heated at 70° C. for 4 h. The solvents were evaporated. After partitioning between EtOAc and water, the organic layer was washed with brine and dried over MgSO4 to give 1-[2-(N-hydroxyimino)cyclohexane-1-sulfonyl]-4-(4-fluorophenyl)piperazine as a white solid (48 mg, 94%): MS (ESI): 356 (MH+).

Workup

  1. customThe solvents were evaporated
  2. customAfter partitioning between EtOAc and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-14232ca70d8c438686b0a4bf7bf41588
Source dataset
uspto-grants-2008_03
Patent number
US07342020B2

Reaction notes

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