Piperazine → 7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-(9-piperazinylnonyl)-3-methylchroman

HRID 1792289Notes

Reaction equation

HRID 1792289 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH2:32][O:33][CH3:34])=[CH:28][CH:29]=3)[O:24][CH2:23][C:22]2([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=2)[CH3:35])(=O)=O)=CC=1.[NH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.[OH-].[Na+]>O1CCOCC1>[CH3:34][O:33][CH2:32][O:31][C:27]1[CH:26]=[C:25]2[C:30]([CH:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)[C:22]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=3)([CH3:35])[CH2:23][O:24]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 154817609-{7-(Methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman-4-yl}nonyl 4-methylbenzenesulfonate

Product 1

HCID 220331067-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-(9-piperazinylnonyl)-3-methylchromanYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9-{7-(Methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman-4-yl}nonyl 4-methylbenzenesulfonate (540 mg, 0.843 mmol) and piperazine (2.2 g, 25.5 mmol) were dissolved in dioxane and then the mixture was refluxed for 2 hours. The mixture was cooled down to room temperature, basified to pH 13 using 5N-NaOH, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the organic solvent was removed under reduced pressure. The concentrate was subjected to column chromatography (methanol) to give 380 mg (yield: 81%, (3RS,4RS):(3RS,4SR)=5:4) of the title compound as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eb6b609ad68141eda11b3cb0a92c7fe2
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…