Bromocyclopentane → HCID 131721174, compound

HRID 1418308Notes

Reaction equation

HRID 1418308 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[C:13]2=[CH:14][CH2:15][CH2:16][CH2:17][N:12]2[C:11]1=[O:20].[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[C:13]2=[CH:14][CH2:15][CH2:16][CH2:17][N:12]2[C:11]1=[O:20]

Participants

6

Reactant 4

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 131721169HCID 131721169, compound

Product 1

HCID 131721174HCID 131721174, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (10 mL) solution of 2-(2-chloro-4-methyl-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.34 g, 1.11 mmol), cyclopentylbromide (0.13 mL, 1.22 mmol) and potassium carbonate (0.15 g, 1.11 mmol) was stirred for 4 hours under reflux. A saturated ammonium chloride solution (20 mL) was added to the resulting mixture and the organic layer was separated. The aqueous layer was extracted with diethyl ether (10 mL×2 times), and the organic layer combined was washed with a saturated sodium chloride solution (40 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2) to obtain a white solid of 2-(2-chloro-5-cyclopentyloxy-4-methylphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.27 g, yield:64.3%).

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether (10 mL×2 times)
  4. washthe organic layer combined was washed with a saturated sodium chloride solution (40 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-718ad704c1a74770b985226ff51721fa
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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