Ethyl Acetate → Cutamesine

HRID 1014952Notes

Reaction equation

HRID 1014952 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:17][CH2:16]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[OH-].[Na+].C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:19][CH2:20]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 99549411-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine--hydrogen chloride (1/2)

Product 1

HCID 9907323CutamesineYield 93.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (1.06 g, 2.40 mmol) in THF (5 mL) is added a solution of sodium hydroxide (1N, 6 mL). To the resulting solution is added ethyl acetate and brine. The organic layer is separated, filtered through silica gel, dried over anhydrous sodium sulfate, concentrated, and dried to give 0.829 g of 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine as a light brown solid.

Workup

  1. customThe organic layer is separated
  2. filtrationfiltered through silica gel
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-722923559f4c4364a9b5be0e338215c9
Source dataset
uspto-grants-2011_07
Patent number
US07985751B2

Reaction notes

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