Triethylamine → 1-{3-[4-(3-Trifluoromethyl-4-chlorobenzyl)piperazin-1-yl]propyl}-3-n-hexylurea dihydrochloride

HRID 543187Notes

Reaction equation

HRID 543187 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][Cl:26].C(N(CC)CC)C>C(O)C>[ClH:26].[ClH:26].[F:31][C:21]([F:20])([F:32])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][N:4]1[CH2:3][CH2:2][N:1]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130942621-Chloro-4-(chloromethyl)-2-(trifluoromethyl)benzeneHCID 571432471-(3-Piperazinylpropyl)-3-n-hexylurea

Product 1

HCID 136067271-{3-[4-(3-Trifluoromethyl-4-chlorobenzyl)piperazin-1-yl]propyl}-3-n-hexylurea dihydrochlorideYield 115.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-piperazinylpropyl)-3-n-hexylurea (2.7 g; 10 mmole), 3-trifluoromethyl-4-chloro-benzyl chloride (2.29 g; 10 mmole), triethylamine (1.01 g; 10 mmole) and ethanol (30 ml) was refluxed for 3 hours. The solvent was evaporated in vacuo, and water was added to the residue. The product was extracted with ether, and the extract was dried (sodium sulfate) and concentrated. Precipitation of the oily residue with ethereal hydrochloric acid, followed by recrystallization from alcohol, provided the title compound (3.1 g; 58% yield) as colorless crystals, m.p. 216°-219° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was evaporated in vacuo, and water
  3. additionwas added to the residue
  4. extractionThe product was extracted with ether
  5. dry with materialthe extract was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customPrecipitation of the oily residue with ethereal hydrochloric acid
  8. customfollowed by recrystallization from alcohol

Sources & evidence

ORD record
ord-ec5e8acdc7ad4825a7617784dd8cf890
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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