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

HRID 1790518Notes

Reaction equation

HRID 1790518 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:24][C:25](=O)[CH3:26])[CH:21]=4)[C:16](C=O)=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.NO.[C:35]([O-])(=[O:37])[CH3:36].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][N:24]5[CH2:25][CH2:26][CH2:36][C:35]5=[O:37])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 220380151-[1-(4-Fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole

Product 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoleYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A liquid mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole (0.09 g) obtained in Example 370, hydroxylamine hydrochloride (0.02 g) and anhydrous sodium acetate (0.03 g) in methanol (10 ml) was stirred at room temperature for 1 hr. Then the reaction mixtures were concentrated and the residue was partitioned between ethyl acetate (20 ml) and a 1 N aqueous solution (10 ml) of sodium hydroxide. The ethyl acetate layer was washed successively with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. Then the residue was crystallized from ether/hexane, collected by filtration, washed with hexane and dried to give the title compound (0.08 g) as a pale yellow powder (yield: 88.5%).

Workup

  1. customThen the reaction mixtures
  2. concentrationwere concentrated
  3. customthe residue was partitioned between ethyl acetate (20 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
  7. customThen the residue was crystallized from ether/hexane
  8. filtrationcollected by filtration
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-9d1a8770810041799eef5f2768e408fc
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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