Hydrochloric Acid → 56915-77-6

HRID 885828Notes

Reaction equation

HRID 885828 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2C#N)[CH2:5][CH2:4]1.[NH4+].[OH-].C[Mg]Br.C([O:24][CH2:25][CH3:26])C.Cl>O.C1(C)C=CC=CC=1>[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:13][CH:14]=[CH:15][C:16]=2[C:25](=[O:24])[CH3:26])[CH2:5][CH2:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14923Ammonium HydroxideHCID 54593279HCID 54593279, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 2140456756915-77-6Yield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4-methyl-piperazin-1-yl)-benzonitrile hydrochloride (2.16 g, 9.1 mmol) in H2O was brought to basic conditions with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4, and evaporated in vacuo. The product obtained (1.77 g, 8.80 mmol) was dissolved in 30 ml of toluene and added under nitrogen atmosphere to a solution of 3 M methyl magnesium bromide in diethyl ether (8.79 ml, 26.38 mmol). The resulting suspension was heated under reflux for 4 hours. The reaction was cooled down to 0° C., acidified with 10% HCl, and then heated under reflux for 1 hour. The two phases were separated and the aqueous phase was extracted with AcOEt, then brought to basic conditions with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated in vacuo to dryness. The crude product was purified by flash chromatography (DCM:MeOH:NH3 98:2:0.2) to obtain 1.62 g of 1-[2-(4-methyl-piperazin-1-yl)-phenyl]-ethanone.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe product obtained (1.77 g, 8.80 mmol)
  5. temperatureThe resulting suspension was heated
  6. temperatureunder reflux for 4 hours
  7. temperatureheated
  8. temperatureunder reflux for 1 hour
  9. customThe two phases were separated
  10. extractionthe aqueous phase was extracted with AcOEt
  11. extractionextracted with DCM
  12. dry with materialThe organic phase was dried over Na2SO4
  13. concentrationconcentrated in vacuo to dryness
  14. customThe crude product was purified by flash chromatography (DCM:MeOH:NH3 98:2:0.2)

Sources & evidence

ORD record
ord-bc350485498c46dc854e2b113071ef44
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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