Sodium Hydroxide → HCID 68141719, compound

HRID 1730951Notes

Reaction equation

HRID 1730951 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]1([CH2:23][CH2:24]Cl)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[ClH:16].[N:17]1([CH:23]([C:14]2[C:13]([Cl:16])=[CH:12][CH:11]=[C:10]3[C:15]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][NH:9]3)[CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 748271-(2-Chloroethyl)piperidineHCID 6151185-Chloro-3-phenyl-1H-indazole

Product 1

HCID 68141719HCID 68141719, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
70 °C

Procedure

3-Phenyl-5-chloroindazole (4.57 g), piperidinoethyl chloride (3.6 g), and triethylbenzylammonium chloride (0.5 g) were added to 50% aqueous sodium hydroxide solution (5 ml) followed by stirring at 70° C for 1 hour. After completion of the reaction, the mixture was extracted with benzene and the extract was washed with water, dried over sodium sulfate and concentrated. The residue was treated with ethanol-hydrochloric acid to obtain 4.3 g of 1-piperidinoethyl-3-phenyl-5-chloroindazole hydrochloride having a melting point between 230°-235° C after recrystallization from acetone.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with benzene
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. additionThe residue was treated with ethanol-hydrochloric acid

Sources & evidence

ORD record
ord-a957e3923ccb414fb7ac64aa465d1c9e
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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