4-Tert-Butylaniline → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-t-butylphenyl)urea dihydrochloride

HRID 1380211Notes

Reaction equation

HRID 1380211 reaction equation
I[CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[C:8]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].[Cl:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>CCOCC.C(O)C>[ClH:19].[ClH:19].[Cl:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:16][C:15]3[CH:14]=[CH:13][C:12]([C:8]([CH3:11])([CH3:9])[CH3:10])=[CH:18][CH:17]=3)=[O:7])[CH2:27][CH2:26]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 698614-Tert-ButylanilineHCID 1348264-ChlorobenzylpiperazineHCID 516892Sodium BicarbonateHCID 22625113HCID 22625113, compound

Product 1

HCID 136067121-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-t-butylphenyl)urea dihydrochlorideYield 108.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-iodopropyl isocyanate (4.22 g; 20 mmole) in ether (25 ml) was added to a solution of 4-t-butylaniline (2.98 g; 20 mmole) in ether (25 ml), and the resulting solution refluxed for 3 hours. After removal of the solvent, 4-chlorobenzylpiperazine (4.18 g; 20 mmole) in ethanol (50 ml) was added and the resulting solution refluxed for 24 hours. Aqueous sodium bicarbonate was added to the mixture and the product was extracted with methylene chloride, dried (sodium sulfate), and the salt precipitated with ethereal hydrochloric acid. Recrystallization several times with ethanol provided the title compound (3.73 g; 33% yield) as colorless crystals, m.p. 240°-241° C.

Workup

  1. temperaturethe resulting solution refluxed for 3 hours
  2. additionwas added
  3. temperaturethe resulting solution refluxed for 24 hours
  4. extractionthe product was extracted with methylene chloride
  5. dry with materialdried (sodium sulfate)
  6. customthe salt precipitated with ethereal hydrochloric acid
  7. customRecrystallization several times with ethanol

Sources & evidence

ORD record
ord-81d29d6b1ea449a2a0a9c5614539f009
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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