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

HRID 1895900Notes

Reaction equation

HRID 1895900 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:17][CH2:16][CH:15]([O:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.O.NN>C(O)C>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:13][CH2:14][CH:15]([O:18][NH2:19])[CH2:16][CH2:17]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=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 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (4.85 g, 10.0 mmol) and hydrazine monohydrate (550 mg, 11.0 mmol) in ethanol (30 ml) was stirred at room temperature for 30 minutes. The resulting solid was filtered off and concentrated in vacuo. The residue was triturated with diethyl ether (80 ml), and the resulting solid was filtered off again and concentrated in vacuo to give O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (3.00 g, 93%) as a white solid: LCMS: 325 [M+1]+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether (80 ml)
  4. filtrationthe resulting solid was filtered off again
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45e1dd13ad254db988078eb49b10f0a0
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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