Hydroxylamine → HCID 11633089, compound

HRID 1008771Notes

Reaction equation

HRID 1008771 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14](/[CH:17]=[CH:18]/[C:19]#[C:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:28][OH:29]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([NH:28][OH:29])[C:19]#[C:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 11710722HCID 11710722, compound

Product 1

HCID 11633089HCID 11633089, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(4-fluorophenyl)-4-{[(1E)-5-phenyl-1-penten-3-ynyl]sulfonyl}piperazine (155 mg; 0.40 mmol) in THF (8 mL) was added hydroxylamine (0.71 mL; 12.1 mmol). The reaction mixture was heated at 60° C. for 1 h. It was then diluted with EtOAc, washed with brine, dried over magnesium sulfate, filtrated and concentrated. Purification of the crude (135 mg) by flash chromatography on silica gave the title compound (50 mg, 30% yield). HPLC, Rt: 3.84 min (purity: 94.5%). LC/MS, M+(ESI): 418.3, M−(ESI): 416.2. 1H NMR (CDCl3) δ: 7.22-7.31 (m, 5H), 7.01 (m, 4H), 4.33 (m, 1H), 3.62 (d, J=1.9 Hz, 2H), 3.53-3.60 (m, 5H), 3.20-3.27 (m, 5H). 1H NMR (CDCl3) δ: 7.30 (m, 5H), 6.95 (m, 4H), 6.32 (d, J=15.6 Hz, 1H), 6.07 (dt, J=16.1, 7.4 Hz, 1H), 3.90 (s, 2H), 3.78 (d, J=6.6 Hz, 2H), 3.22 (m, 4H), 2.91 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customPurification of the crude (135 mg) by flash chromatography on silica

Sources & evidence

ORD record
ord-98cfbb5272dd437596bee5e4e7b31342
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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