Sodium Hydroxide → HCID 68541591, compound

HRID 1993647Notes

Reaction equation

HRID 1993647 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][CH2:9]2)[CH:3]=1.[N+:20]([O-])([O-:22])=[O:21].[K+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[C:7]([N+:20]([O-:22])=[O:21])=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:10][CH2:9]2)[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 685369901-Propanone, 1-[4-(4-chloro-2-pyridinyl)-1-piperazinyl]-2,2-dimethyl-

Product 1

HCID 68541591HCID 68541591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-[4-(4-chloro-pyridin-2-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one (1.6 mmol, 0.4 g) in sulfuric acid (2.3 mL) and cool the solution down to 0° C. Add potassium nitrate (1.6 mmol, 0.2 g) and stir the mixture allowing to reach room temperature overnight. Dilute the mixture with water and add sodium hydroxide 10% until basic pH. Extract in ethyl acetate. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue of 1-[4-(4-chloro-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one. Subject residue to silica gel chromatography eluting with a mixture hexanes/ethyl acetate as (from 30% up to 60%). MS(ES): m/z=327 [M+H].

Workup

  1. extractionExtract in ethyl acetate
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1aac11783ea44614b8182eb9d1330e29
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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