Hydrochloric Acid → HCID 13565854, compound

HRID 980734Notes

Reaction equation

HRID 980734 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-(acetyl-cyclopropylamino)-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 1.0 N 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-17ade5cf42294f7090345f559ce14096
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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