Ammonium formate → HCID 18414104, compound

HRID 428536Notes

Reaction equation

HRID 428536 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-407dbe898f1446a5b05cbebab20a7580
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

Loading…