Acetic Acid → HCID 178419920, compound

HRID 652161Notes

Reaction equation

HRID 652161 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. extractionThe aqueous phase was 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-9070a058386b4cdca359de4c4b7dfba5
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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