Hydrochloric Acid → HCID 14032599, compound

HRID 1722162Notes

Reaction equation

HRID 1722162 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>O>[Cl:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[N:11][N:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14032652HCID 14032652, compound

Product 1

HCID 14032599HCID 14032599, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-acetyl-4-(6-chloro-1-phenyl-1H-indazol-3-yl)piperidine (8.2 g; 0.023 mol) of Example 95(b) was stirred and refluxed with 6N HCl (75 ml) for 5 hours. The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate was evaporated and filtered. The aqueous solution was chilled, stirred and 50% NaOH was added dropwise. The resultant basic mixture was extracted with ethyl acetate and the organic extract was washed and dried and then concentrated to yield an oil which solidified on standing to yield 5.7 g of 6-chloro-1-phenyl-3-(4-piperidinyl)-1H-indazole.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe ethyl acetate was evaporated
  3. filtrationfiltered
  4. temperatureThe aqueous solution was chilled
  5. stirringstirred
  6. addition50% NaOH was added dropwise
  7. extractionThe resultant basic mixture was extracted with ethyl acetate
  8. extractionthe organic extract
  9. washwas washed
  10. customdried
  11. concentrationconcentrated
  12. customto yield an oil which

Sources & evidence

ORD record
ord-6eb7adf05bba4cd3a290d9fe4583fcfc
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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