Hydrazine hydrate (1:1) → HCID 67118420, compound

HRID 1895947Notes

Reaction equation

HRID 1895947 reaction equation
[F:1][C:2]([F:32])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([N:13]3[CH2:18][CH2:17][CH:16]([O:19][N:20]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:15][CH2:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O.NN>C(Cl)Cl>[F:32][C:2]([F:1])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([N:13]3[CH2:14][CH2:15][CH:16]([O:19][NH2:20])[CH2:17][CH2:18]3)[CH2:11][CH2:12]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67118434HCID 67118434, compound

Product 1

HCID 67118420HCID 67118420, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 2-(1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-yloxy)isoindoline-1,3-dione (995 mg, 2.08 mmol) and hydrazine monohydrate (0.304 ml, 6.25 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 3 hours. The resulting solid was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 45/55 to 75/25) to give O-(1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-yl)hydroxylamine (580 mg, 88%) as pale yellow oil.

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (ethyl acetate/hexane: 45/55 to 75/25)

Sources & evidence

ORD record
ord-2d1a7e87ae4148b2991bdfecce88cebc
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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