Sodium Methoxide → HCID 14032654, compound

HRID 1382608Notes

Reaction equation

HRID 1382608 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]#[N:23])[CH2:18][CH2:17]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][O-:25].[Na+]>CO>[CH3:24][O:25][C:22]([N:19]1[CH2:18][CH2:17][CH:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:21][CH2:20]1)=[NH:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14032637HCID 14032637, compound

Product 1

HCID 14032654HCID 14032654, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(1-phenyl-1H-indazol-3-yl)piperidine-1-carbonitrile of Example 73 (4.0 g, 0.013 moles) and sodium methoxide (3 ml of 25% sodium methoxide in methanol, 0.013 moles) in methanol (30 ml) was warmed to effect solution and then stirred at ambient temperature for 16 hours. The solvent was removed which left an oil (4.5 g). The oil was dissolved in ether, washed with H2O, and dried (MgSO4). Removal of the ether left an oil which began to crystallize upon standing. Crystallization was enhanced by triturating the oil with hexane which produced 3.5 g of product. The product was recrystallized twice from hexane yielding 2.31 g (52%) of 4-(1-phenyl-1H-indazol-3-yl)piperidine-1-carboximidic acid methyl ester, mp 80°-83° C.

Workup

  1. temperaturewas warmed
  2. customThe solvent was removed which
  3. waitleft an oil (4.5 g)
  4. dissolutionThe oil was dissolved in ether
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. customRemoval of the ether
  8. waitleft an oil which
  9. customto crystallize
  10. customCrystallization
  11. customby triturating the oil with hexane which

Sources & evidence

ORD record
ord-8d553345dd5c4f04a151b0e6b4088571
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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