Hydroxyamine hydrochloride → HCID 74017951, compound

HRID 501332Notes

Reaction equation

HRID 501332 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[F:26])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[F:26])=[N:28][OH:29])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23112486HCID 23112486, compound

Product 1

HCID 74017951HCID 74017951, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of (1-benzyl-piperidin-4-yl)-(2-fluoro-4-trifluoromethyl-phenyl)-methanone (5.0 g, 13.66 mmol), hydroxylamine hydrochloride (1.1 g, 16.39 mmol) and pyridine (50 mL) was stirred at room temperature overnight when the mixture was distilled to remove pyridine (35 mL). The solid residue was washed with heptane then ether. The resulting solid was partitioned between a saturated solution of NaHCO3 and EtOAc. The organic layer was dried (MgSO4) filtered and evaporated. The solid residue was washed with 3:1 heptane/EtOAc and dried under vacuum to obtain 2.1 g (40%) of the desired product as a white solid.

Workup

  1. distillationwas distilled
  2. customto remove pyridine (35 mL)
  3. washThe solid residue was washed with heptane
  4. customThe resulting solid was partitioned between a saturated solution of NaHCO3 and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. washThe solid residue was washed with 3:1 heptane/EtOAc
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e39c9baf2ee042b985576f27e3b6fbec
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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