Tetrahydrofuran → HCID 57420348, compound

HRID 1689880Notes

Reaction equation

HRID 1689880 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-ebf1308c3d4f478581c2724ae300a192
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

Loading…