Hydrochloric Acid → N,N-Diethylbenzamide

HRID 1460098Notes

Reaction equation

HRID 1460098 reaction equation
Cl.S(Cl)(Cl)=[O:3].[CH3:6][C@H:7]1CN[C@H:10](C)[CH2:9][NH:8]1.[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:7]([N:8]([CH2:9][CH3:10])[C:20](=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 24386Thionyl ChlorideHCID 2206722,5-Dimethylpiperazine, trans-

Product 1

HCID 15542N,N-Diethylbenzamide

Procedure

The product (25 mmol) was treated with 2M ethanolic hydrochloric acid (20 mL). The solvent was evaporated and the residue shaken with toluene and evaporated again to remove residual ethanol. The resulting yellow solid was suspended in dichloromethane, 2.7 mL (37.5 mmol) of thionyl chloride was added, and the mixture was stirred at room temperature for one hour. The solvent was evaporated, and the residue was taken up in toluene and evaporated again to drive off the excess thionyl chloride. The crude product (approximately 25 mmol) was then treated with trans-2,5-dimethylpiperazine (28.5 g, 0.25 mol) in toluene as described in Example1. The product was purified by chromatography on silica gel (Waters Prep 500, dichloromethane:ethanol:triethylamine/100:1.5-3:0.1), to give 3.71 g (38%) of (±)-4-α-(trans-2,5-dimethyl-1-piperazinyl)-3-aminobenzyl)-N,N-diethylbenzamide as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. customevaporated again
  3. customto remove residual ethanol
  4. stirringthe mixture was stirred at room temperature for one hour
  5. customThe solvent was evaporated
  6. customevaporated again
  7. customThe product was purified by chromatography on silica gel (Waters Prep 500, dichloromethane:ethanol:triethylamine/100:1.5-3:0.1)

Sources & evidence

ORD record
ord-2fd51b6e4a05434180fb8390bd966879
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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