Hydrazine hydrate (1:1) → HCID 67118448, compound

HRID 1895909Notes

Reaction equation

HRID 1895909 reaction equation
O.NN.[F:4][C:5]([F:35])([F:34])[O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][N:23]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(O)C>[F:35][C:5]([F:4])([F:34])[O:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][NH2:23])[CH2:18][CH2:17]2)(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67118409HCID 67118409, compound

Product 1

HCID 67118448HCID 67118448, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine monohydrate (636 mg, 10.8 mmol) was added to a solution of 2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (4.23 g, 9.00 mmol) in ethanol (40 ml) and stirred at 50° C. for 2 hours. 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-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yl)hydroxylamine (2.63 g, 86%) as a white solid: LCMS: 341 [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-79cce8794d3c410c8df67db562a6d69e
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

Loading…