Hydrochloric Acid → HCID 13565854, compound

HRID 868129Notes

Reaction equation

HRID 868129 reaction equation
C([N:4]([CH:23]1[CH2:25][CH2:24]1)[C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:8]([F:22])=[CH:7][CH:6]=1)(=O)C.Cl>CO>[CH:23]1([NH:4][C:5]2[N:10]=[C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:8]([F:22])=[CH:7][CH:6]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13823371HCID 13823371, compound

Product 1

HCID 13565854HCID 13565854, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 21.9 g (63 mmole) of 4-[6-(acetylcyclopropylamino)-3-fluoro-2-pyridinyl]-1-piperazinecarboxylic acid, ethyl ester, 170 ml of 15% hydrochloric acid and 235 ml of methanol was refluxed for one hour and allowed to stir at room temperature for 18 hours. The methanol was removed in vacuo and the aqueous acid was made basic with 1.0N sodium hydroxide to pH 10.5. The mixture was extracted with chloroform, the chloroform layer washed with water, dried over magnesium sulfate, and evaporated in vacuo to give 17.6 g of the title compound, mp 68°-70° C.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionThe mixture was extracted with chloroform
  3. washthe chloroform layer washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-04cff92e4d4d4e45a3c07896447f69fa
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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