Hydrochloric Acid → 1-[4-(Dimethylaminomethyl)benzoyl]-4-(3,3-diphenylpropyl)homopiperazine

HRID 2119347Notes

Reaction equation

HRID 2119347 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.[CH3:27][N:28]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]([C:35](OC)=[O:36])=[CH:33][CH:32]=1)[CH3:29].Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.CCCCCC>[CH3:29][N:28]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:35]([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:12]2)=[O:36])=[CH:39][CH:40]=1)[CH3:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12361573Methyl 4-((dimethylamino)methyl)benzoateHCID 16682925TrimethylaluminumHCID 234410351-(3,3-Diphenyipropyl)homopiperazine

Product 1

HCID 698911161-[4-(Dimethylaminomethyl)benzoyl]-4-(3,3-diphenylpropyl)homopiperazine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

The resulting 1-(3,3-diphenylpropyl)homopiperazine was dissolved in 3 mL of toluene under argon, followed by adding 0.65 mL of a 15% trimethylaluminum solution in hexane. The mixture was stirred at room temperature for 15 minutes, mixed with 187 mg of methyl 4-(dimethylaminomethyl)benzoate, stirred at 60° C. for 22 hours. The mixture was cooled to room temperature, mixed with 2N hydrochloric acid, and stirred. 20 mL of aqueous 2N sodium hydroxide was added and the mixture was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined, washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate/methanol 6:4) to obtain 234 mg of the titled compound. This was treated with a hydrogen chloride solution in ether, the solvent was removed under reduced pressure and the residue was dried to give the hydrochloride salt of the titled compound.

Workup

  1. stirringstirred at 60° C. for 22 hours
  2. temperatureThe mixture was cooled to room temperature
  3. stirringstirred
  4. extractionthe mixture was extracted with 20 mL×2 of ethyl acetate
  5. washwashed with 20 mL of saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica gel, ethyl acetate/methanol 6:4)

Sources & evidence

ORD record
ord-3a1977b974ff49ab9d2772934b785a16
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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