Pipecolic Acid → HCID 13281222, compound

HRID 1903650Notes

Reaction equation

HRID 1903650 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]=[C:10]=[O:11])=[C:4]([F:12])[CH:3]=1.[NH:13]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:14]1[C:15](O)=[O:16].[OH-].[Na+]>ClC1C=CC=CC=1.O>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:15](=[O:16])[CH:14]3[CH2:18][CH2:19][CH2:20][CH2:21][N:13]3[C:10]2=[O:11])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 3

HCID 849Pipecolic AcidHCID 14798Sodium HydroxideHCID 20466345HCID 20466345, compound

Product 1

HCID 13281222HCID 13281222, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
20 °C

Procedure

4-Bromo-2-fluoro-5-hydroxyphenyl isocyanate (3 g) was dissolved in chlorobenzene (5 ml), and a solution of pipecolic acid (1.7 g) and sodium hydroxide (0.56 g) in water (5 ml) was added thereto, followed by stirring at room temperature (ca. 20° C.) overnight. The aqueous layer was washed with ether, made acidic with an aqueous hydrochloric acid solution and heated under reflux for 2 hours. After allowed to cool, the resulting mixture was extracted with methylene chloride (300 ml). The extract was washed with sodium bicarbonate solution, dried and concentrated. The residue was recrystallized from ether to give 1.75 g of 2-(4-bromo-2-fluoro-5-hydroxyphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-1,3(2H,8aH)-dione. M.P., 196°-199° C.

Workup

  1. washThe aqueous layer was washed with ether
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. temperatureto cool
  5. extractionthe resulting mixture was extracted with methylene chloride (300 ml)
  6. washThe extract was washed with sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-ae9305f157aa488b91ff8548c0ebcc9f
Source dataset
uspto-grants-1984_03
Patent number
US04437877

Reaction notes

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