Hydroxylamine → HCID 88996196, compound

HRID 331522Notes

Reaction equation

HRID 331522 reaction equation
[NH2:1][OH:2].[OH2:3].[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O)[CH2:15][CH2:14][N:13]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:8][CH:7]=1)=O>C(O)C>[OH:2]/[N:1]=[CH:4]/[C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:3])[CH2:15][CH2:14][N:13]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 86680967HCID 86680967, compound

Product 1

HCID 88996196HCID 88996196, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine 50% solution in water (236.5 μL of 50% w/v, 3.580 mmol) was added to a stirred solution of di tert-butyl 2-(4-formylphenyl)piperazine-1,4-dicarboxylate (699 mg, 1.790 mmol) in ethanol (20 mL) at ambient temperature. Stirred at ambient temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue taken up in water and extracted with ethyl acetate (×3). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a white foam. Taken onto the next step as is (725.8 mg, assume 100% yield).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white foam

Sources & evidence

ORD record
ord-28f2cdff51d64aa6ab23a7cc4aa57719
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

Loading…