Hydrazine hydrate (1:1) → O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

HRID 1895904Notes

Reaction equation

HRID 1895904 reaction equation
O.NN.[F:4][C:5]([F:34])([F:33])[C:6]1[CH:7]=[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH:18]([O:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1>C(O)C>[F:34][C:5]([F:4])([F:33])[C:6]1[CH:7]=[C:8]([S:12]([N:15]2[CH2:16][CH2:17][CH:18]([O:21][NH2:22])[CH2:19][CH2:20]2)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 671183862-(1-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione

Product 1

HCID 67118429O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamineYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (250 mg, 4.24 mmol) was added to a solution of 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (1.02 g, 2.24 mmol) in ethanol (10 ml) and stirred at room temperature for 30 minutes. The resulting solid was filtered off and concentrated in vacuo. The residue was triturated with diethyl ether (30 ml), and the resulting solid was filtered off again and concentrated in vacuo to give O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (720 mg, 94%) as a white solid: LCMS: 343 [M+1]+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether (30 ml)
  4. filtrationthe resulting solid was filtered off again
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32d0a415837849fa861e8ad8bd22954a
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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