Hydroxylamine → HCID 11565825, compound

HRID 1008772Notes

Reaction equation

HRID 1008772 reaction equation
[CH:1](/[S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6])=[CH:2]\[C:3]#[CH:4].[NH2:20][OH:21]>C1COCC1>[OH:21][NH:20][CH:2]([C:3]#[CH:4])[CH2:1][S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 11680688HCID 11680688, compound

Product 1

HCID 11565825HCID 11565825, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-[(1E)-1-buten-3-ynylsulfonyl]-4-(2-pyridinyl)piperazine (30 mg; 0.11 mmol; 1.00 eq.) in THF (3 mL) was added an aq. solution of hydroxylamine (50%, 0.10 mL; 1.62 mmol; 15.0 eq.) and the resulting reaction mixture was stirred at 60° C. for 4 h. Evaporation of the solvents (rotavap gave an oil). Purification on silicagel (50/50 up to 70/30 AcOEt-c-Hex) a colorless oil (15 mg, 44% yield). LC/MS, M+ (ESI): 311.1, M−(ESI): 311.1, M− (ESI): 309.0.

Workup

  1. customthe resulting reaction mixture
  2. customEvaporation of the solvents (rotavap
  3. customgave an oil)

Sources & evidence

ORD record
ord-2c08ffcef1694e71bf83d25f2b4ccb3b
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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