Hydrochloric Acid → 1-{4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}piperidine-4-carboxylic acid

HRID 735444Notes

Reaction equation

HRID 735444 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([O:31]CC)=[O:30])[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:37])([F:36])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([OH:31])=[O:30])[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:37])([F:35])[F:36])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67021080HCID 67021080, compound

Product 1

HCID 117127041-{4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}piperidine-4-carboxylic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 1-{4-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}piperidine-4-carboxylate (0.06 g, 0.12 mmol) in 5 mL of methanol containing 1 mL of 1 N NaOH was stirred overnight at ambient temperature. The reaction mixture was neutralized with dilute HCl and partitioned with ethyl acetate and H2O. The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was triturated with petroleum ether to give the title compound as an amber solid (0.049 g).

Workup

  1. custompartitioned with ethyl acetate and H2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-d5e13351a56647bb9c6d798e07494070
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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