N,N-Dimethylethylenediamine → N-[2-(Dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide

HRID 1087823Notes

Reaction equation

HRID 1087823 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][N:14]([CH2:16][CH2:17][NH2:18])[CH3:15].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1>O1CCCC1>[CH3:13][N:14]([CH3:15])[CH2:16][CH2:17][NH:18][C:1]([N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=2)[CH2:27][CH2:28]1)=[O:2]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 14763463N-[2-(Dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 6.3 g (0.04 mole) of 1,1'-carbonyldiimidazole in 50 ml of tetrahydrofuran (THF) was added a solution of 3.4 g (0.04 mole) of unsym-dimethylethylenediamine in 75 ml of THF and the reaction mixture was stirred at ambient temperature for 1.5 hr. A solution of 7.0 g (0.04 mole) of 1-(4-fluorophenyl)piperazine in 50 ml of THF was added and the reaction mixture was heated at reflux for 20 hr. The solution was concentrated under reduced pressure and the residue was dissolved in 150 ml of benzene. The solution was washed thrice with 50 ml portions of water and once with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil which solidified. After trituration with petroleum ether (30°-60° C.), the collected solid was recrystallized from isopropyl alcohol/hexane to yield 7.8 g (68%) of title compound as a crystalline, white solid, m.p. 99°-101° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 hr
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 150 ml of benzene
  5. washThe solution was washed thrice with 50 ml portions of water
  6. dry with materialonce with brine, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil which
  9. customAfter trituration with petroleum ether (30°-60° C.), the collected solid was recrystallized from isopropyl alcohol/hexane

Sources & evidence

ORD record
ord-fe958f37e2414cd2989601eba5ae1215
Source dataset
uspto-grants-1990_10
Patent number
US04960776

Reaction notes

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