Morpholine → 4-(4-Fluorophenyl)-2-(3-morpholinopropyl)-3-(4-pyridyl)pyrrole

HRID 412082Notes

Reaction equation

HRID 412082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:10]([CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[C:10]([CH2:13][CH2:14][CH2:15][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 185375134-(4-Fluorophenyl)-2-(3-mesyloxypropyl)-3-(4-pyridyl)pyrrole

Product 1

HCID 185375124-(4-Fluorophenyl)-2-(3-morpholinopropyl)-3-(4-pyridyl)pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(4-fluorophenyl)-2-(3-mesyloxypropyl)-3-(4-pyridyl)pyrrole (0.25 g, 0.0007 mol) was refluxed for 16 hours in CH2Cl2 (50 mL) and morpholine (0.25 mL). The solution was cooled and diluted with CH2Cl2 (˜100 mL), then washed with H2O (3×50 mL). The organics were dried over Na2SO4 and evaporated in vacuo to give an oil. This oil was purified on SiO2 eluting with 10% MeOH in CH2Cl2 to give 4-(4-fluorophenyl)-2-(3-morpholinopropyl)-3-(4-pyridyl)pyrrole isolated as a solid (0.088 g, 36% yield). 1HNMR (DMSO-d6) δ 11.12 (1H, s, NH), 8.42 (2H, d), 7.05 (6H, m), 6.95 (1H, d), 3.55 (4H, t), 2.62 (2H, t), 2.29 (6H, m), 1.71 (2H, m).

Workup

  1. temperatureThe solution was cooled
  2. washwashed with H2O (3×50 mL)
  3. dry with materialThe organics were dried over Na2SO4
  4. customevaporated in vacuo
  5. customto give an oil
  6. customThis oil was purified on SiO2 eluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-ada3241883bf4300b8869dca28f5f126
Source dataset
uspto-grants-2003_05
Patent number
US06562843B1

Reaction notes

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