Ammonium formate → 4-(6-Methoxy-2-methylquinolin-8-yl)piperazine

HRID 428533Notes

Reaction equation

HRID 428533 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([O:25][CH3:26])[CH:17]=[C:18]3[C:23]=2[N:22]=[C:21]([CH3:24])[CH:20]=[CH:19]3)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].CCOC(C)=O.CCCCCC>CO.[Pd]>[CH3:26][O:25][C:16]1[CH:17]=[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]=[C:21]([CH3:24])[CH:20]=[CH:19]2

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 18414093HCID 18414093, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 184141504-(6-Methoxy-2-methylquinolin-8-yl)piperazineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-4-(6-methoxy-2-methylquinolin-8-yl)piperazine (0.527 g, 1.52 mmol), 10% Pd/C (0.20 g), and ammonium formate (0.96 g, 15.2 mmol) in methanol (10 mL) were heated at reflux under N2 for 3 hours. TLC analysis (35% EtOAc/hexane) indicated only a trace of starting material remained. After cooling to room temperature, the reaction was filtered through celite, washing with excess methanol. The filtrate was concentrated, diluted with CH2Cl2 (50 mL), and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 0.37 g (95%) of the title compound as a yellow oil, which was used in the subsequent reaction without purification.

Workup

  1. temperaturewere heated
  2. temperatureat reflux under N2 for 3 hours
  3. filtrationthe reaction was filtered through celite
  4. washwashing with excess methanol
  5. concentrationThe filtrate was concentrated
  6. additiondiluted with CH2Cl2 (50 mL)
  7. washwashed with saturated aqueous NaHCO3
  8. extractionThe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  9. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1234166dc00344a789f5f352bdf2b2ae
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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