Acetic Acid → HCID 178419920, compound

HRID 2107413Notes

Reaction equation

HRID 2107413 reaction equation
COC([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH2:7][CH2:6]1)=N.C(O)(=O)C>O>[NH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1784968134-(1H-indazol-3-yl)piperidine-1-carboximidic acid methyl ester

Product 1

HCID 178419920HCID 178419920, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.7 g of 4-(1H-indazol-3-yl)piperidine-1-carboximidic acid methyl ester and 80% of acetic acid was heated under reflux for 48 hrs. The reaction mixture was cooled and poured into water The aqueous phase was extracted with ether and then made basic by the slow addition of a 50% aqueous sodium hydroxide solution. A solid separated from the solution. The solid was collected and dried. Recrystallization from ethanol yielded 1.7 g (46%) of product. Concentration of the mother liquors from this and another experiment gave additional product mp 213°-215° C.

Workup

  1. temperatureunder reflux for 48 hrs
  2. temperatureThe reaction mixture was cooled
  3. extractionwas extracted with ether
  4. additionmade basic by the slow addition of a 50% aqueous sodium hydroxide solution
  5. customA solid separated from the solution
  6. customThe solid was collected
  7. customdried
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-d4f58dfaef234a58b1ea62b46a84f56b
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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