1-(4-Pyridyl)piperazine → HCID 18918312, compound

HRID 864800Notes

Reaction equation

HRID 864800 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(O)(C)C.Cl>[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:10]=4)[N:5]=[CH:4][CH:3]=3)[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918531HCID 18918531, compound

Product 1

HCID 18918312HCID 18918312, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 4-bromoquinolin-6-yloxyacetate (169 mg) in isopropanol(10 ml) was added 1-(4-pyridyl)piperazine (93 mg) followed by 2 drops of saturated ethereal HCl. The resulting mixture was refluxed for 18 hours. The mixture was filtered and concentrated. Purification by flash column chromatography on silica, eluting with methanol/dichloromethane (10% to 15% v/v in 1% increments) gave methyl 4-[4-(4-pyridyl)piperazin-1-yl]quinolin-6-yloxyacetate (74 mg) as a solid: NMR(d6DMSO) δ3.2-3.4(m,4H), 3.6-3.7(m,4H), 3.75(s, 3H), 5.0(s,2H), 6.95(d,2H), 7.05(d,1H), 7.25(d,1H), 7.45(dd,1H), 7.9(d,1H), 8.25(d,2H), 8.6(d,11H); m/e 379(M+H)+.

Workup

  1. temperatureThe resulting mixture was refluxed for 18 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customPurification by flash column chromatography on silica
  5. washeluting with methanol/dichloromethane (10% to 15% v/v in 1% increments)

Sources & evidence

ORD record
ord-9607a37717f243ab8167b8d625d7658b
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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