2,5-Dimethoxytetrahydrofuran → 4-(Pyrrole-1-yl)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

HRID 2514

Reaction equation

HRID 2514 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.CO[CH:38]1[CH2:42][CH2:41][CH:40](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25](=[O:33])[C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[CH2:21][CH2:20]3)[C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)=[O:7])=[CH:34][CH:35]=2)[CH:38]=[CH:42][CH:41]=[CH:40]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 196899144-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide

Product 1

HCID 196898944-(Pyrrole-1-yl)-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (237.0 mg, 0.50 mmol) was dissolved in acetic acid (5.0 ml), and the solution was mixed with 2,5-dimethoxytetrahydrofuran (0.065 ml, 0.50 mmol) and heated for 1 hour under reflux. After cooling, acetic acid was distilled off under a reduced pressure, the residue was dissolved in ethyl acetate, and the organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 217.0 mg (82,7%) of the title compound in a colorless amorphous form.

Workup

  1. temperatureheated for 1 hour
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. distillationacetic acid was distilled off under a reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried on anhydrous sodium sulfate
  8. distillationThereafter, the solvent was distilled off under a reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-af152361a976447c83199ce000045ab8
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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