Benzene → HCID 18377422, compound

HRID 2301149Notes

Reaction equation

HRID 2301149 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:18])([CH3:17])[C:15]#N)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[CH:24]=[CH:23]C=[CH:21][CH:20]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([CH3:17])([C:15]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[CH3:18])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 25517Ammonium ChlorideHCID 22314812HCID 22314812, compound

Product 1

HCID 18377422HCID 18377422, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In an atmosphere of argon and at room temperature, 2-(4-benzyl-piperazin-1-yl)-2-methyl-propionitrile (820 mg, 3.4 mmol) dissolved in diethyl ether (1.2 ml) and benzene (2.5 ml) was added dropwise to phenylmagnesium bromide ether solution (3.0 M, 2.0 ml, 6.0 mmol), and the mixture after completion of the dropwise addition was stirred for 3.5 hours. The reaction solution was mixed with 10% ammonium chloride aqueous solution (18 ml) and separated into water layer and organic layer. The reaction product was extracted from the organic layer with dilute hydrochloric acid, and then the water layer was neutralized with aqueous ammonia and the reaction product was again extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, the solvent was removed by evaporation under a reduced pressure, and then the thus obtained material was separated and purified by a silica gel column chromatography to obtain 300 mg (1.0 mmol, 30% in yield) of the title compound.

Workup

  1. additionthe mixture after completion of the dropwise addition
  2. customseparated into water layer and organic layer
  3. extractionThe reaction product was extracted from the organic layer with dilute hydrochloric acid
  4. extractionthe reaction product was again extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent was removed by evaporation under a reduced pressure
  8. customthe thus obtained material was separated
  9. custompurified by a silica gel column chromatography
  10. customto obtain

Sources & evidence

ORD record
ord-08d731d930db4724be0b5b5302063e73
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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