Acetic Acid → HCID 178501915, compound

HRID 1722151Notes

Reaction equation

HRID 1722151 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]#N)[CH2:12][CH2:11]2)=[N:2]1.C[O-:19].[Na+].[C:21](O)(=[O:23])C>CO>[CH3:21][O:23][C:16]([N:13]1[CH2:14][CH2:15][CH:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)[CH2:11][CH2:12]1)=[O:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 178511845HCID 178511845, compound

Product 1

HCID 178501915HCID 178501915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of 4-(1H-indazol-3-yl)piperidine-1-carbonitrile (7.9 g, 0.024 mole) in methanol (15 ml) was added 4.9 ml of 25% solution of sodium methoxide in methanol. The solution was stirred at ambient temperature for 16 hours, made neutral to pH paper with glacial acetic acid, and extracted with ether. The aqueous solution was made basic with concentrated NH4OH, and extracted thrice with CH2Cl2 (35 ml). The organic extracts were combined, washed (H2O), dried (MgSO4) and the solvent removed in vacuo to yield 6.6 g of an oil. The oil was triturated with hexane and the resultant solid collected (5.4 g). Recrystallization from CH3CN (twice) yielded 3.5 g (56.8%) of 4-(1H-indazol-3-yl)piperidine-1-carboximidic acid methyl ester having a melting point of 153°-155° C.

Workup

  1. extractionextracted with ether
  2. extractionextracted thrice with CH2Cl2 (35 ml)
  3. washwashed (H2O)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-35074882741642f3af6246d331a48049
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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