Tetrahydrofuran → HCID 57420348, compound

HRID 2353121Notes

Reaction equation

HRID 2353121 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11](C(=O)COC)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][Mg]Br.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>C(Cl)(Cl)Cl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:22]([CH3:23])([CH3:19])[CH2:26][O:25][CH3:24])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 1122381HCID 1122381, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57420348HCID 57420348, compound

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(4-benzyl-piperazin-1-yl)-2-methoxy-ethanone (6.14 g) in dry THF (80 mL) at −10° C. was added zirconium chloride (5.76 g). After 30 minutes methyl magnesium bromide (3.0M solution in ether, 49.6 mL) was added in a dropwise manner. The reaction mixture was allowed to warm to room temperature. After stirring for 1 day, the reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the was solvent removed in vacuo. The resulting residue was purified using flash chromatography to yield 1-benzyl-4-(2-methoxy-1,1-dimethyl-ethyl)-piperazine. Subsequent transfer hydrogenation, using ammonium formate and 10% palladium on carbon in MeOH, furnished the desired compound.

Workup

  1. temperaturethe reaction mixture was cooled
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe was solvent removed in vacuo
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-72db30093a4e48339e1713d4568a3f5b
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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