Ammonium formate → HCID 18414104, compound

HRID 992057Notes

Reaction equation

HRID 992057 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([O:25][CH3:26])[C:17]([CH3:24])=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:26][O:25][C:16]1[C:17]([CH3:24])=[C:18]2[C:23](=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:15]=1)[N:22]=[CH:21][CH:20]=[CH:19]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18414119HCID 18414119, compound

Product 1

HCID 18414104HCID 18414104, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methanol (15mL), 10% Pd/C (0.12 g), 1-benzyl-4-(6-methoxy-5-methylquinolin-8-yl)piperazine (0.8 g, 2.3 mmol), and ammonium formate (0.88 g, 13.9 mmol) were refluxed for 45 minutes. The reaction mixture was filtered through celite and concentrated. The residue was diluted with 1 N aqueous NaOH (50 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with water (50 mL) and brine(50 mL), then were dried over anhydrous Na2SO4, filtered, and concentrated to give 0.52 g (61%) of the title compound as a thick oil. MS (ES) m/z: 258 (M+H+).

Workup

  1. temperaturewere refluxed for 45 minutes
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated
  4. additionThe residue was diluted with 1 N aqueous NaOH (50 mL)
  5. extractionextracted with ethyl acetate (3×75 mL)
  6. washThe combined organic layers were washed with water (50 mL) and brine(50 mL)
  7. dry with materialwere dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3ba35d35d8dd416c83f8d8c5de68ded4
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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