Triethylamine → 4,5-dihydro-4-(1-pentafluoropropionylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one

HRID 619503Notes

Reaction equation

HRID 619503 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]2[CH2:20][C:19]3[N:21]4[C:12](=[CH:13][N:14]=[C:15]4[CH:16]=[CH:17][CH:18]=3)[C:11]2=[O:22])[CH2:5][CH2:4]1.C(N(CC)CC)C.FC(F)(F)C(F)(F)C([O:35][C:36](=O)[C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])=O>C(#N)C>[F:42][C:37]([F:43])([C:38]([F:41])([F:40])[F:39])[C:36]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]2[CH2:20][C:19]3[N:21]4[C:12](=[CH:13][N:14]=[C:15]4[CH:16]=[CH:17][CH:18]=3)[C:11]2=[O:22])[CH2:5][CH2:4]1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67742Pentafluoropropionic anhydrideHCID 211902714,5-dihydro-4-(piperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one dihydrochloride

Product 1

HCID 211901874,5-dihydro-4-(1-pentafluoropropionylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-oneYield 63.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 10 ml of acetonitrile was suspended 687 mg (2.0 mM) of 4,5-dihydro-4-(piperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one dihydrochloride, followed by addition of 2.23 ml (16.0 mM) of triethylamine and 1.97 ml (10.0 mM) of pentafluoropropionic anhydride in the order mentioned. This mixture was stirred at room temperature for 1 hour and the solvent was then distilled off under reduced pressure. The residue was extracted with 50 ml of chloroform and the organic layer was washed with 50 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1) to provide 526 mg (yield 63.2%) of the title compound as light-yellow amorphous substance.

Workup

  1. distillationthe solvent was then distilled off under reduced pressure
  2. extractionThe residue was extracted with 50 ml of chloroform
  3. washthe organic layer was washed with 50 ml of saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1)

Sources & evidence

ORD record
ord-0252bce3457644bbbb16f94f784aa001
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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