Hydroxyamine hydrochloride → 1-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindole

HRID 1790507Notes

Reaction equation

HRID 1790507 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1.Cl.[NH2:28][OH:29].C([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[N:28][OH:29])[CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 220383201-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindole

Product 1

HCID 865844061-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoleYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-formylindole (1.94 g) obtained in Example 348-4), hydroxylamine hydrochloride (0.5 g) and anhydrous sodium acetate (0.55 g) in methanol (60 ml) was stirred at room temperature for 1 hr. Then the reaction mixtures were concentrated and the residue was partitioned between ethyl acetate (150 ml) and a 1 N aqueous solution (30 ml) of sodium hydroxide. The ethyl acetate layer was washed successively with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindole (1.96 g) as an ivory powder (yield: 96.8%).

Workup

  1. customThen the reaction mixtures
  2. concentrationwere concentrated
  3. customthe residue was partitioned between ethyl acetate (150 ml)
  4. washThe ethyl acetate layer was washed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a03bc70265cb4b258a82aa2264d0ca35
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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