Ethanol → 1-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)urea dihydrochloride monohydrate

HRID 543189Notes

Reaction equation

HRID 543189 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:7].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.C(O)C>CCOCC>[OH2:7].[ClH:1].[ClH:17].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)=[O:7])[CH2:31][CH2:32]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 1628731-(3-(4-Chlorophenyl)propyl)piperazineHCID 136067331-(3-Chloropropyl)-3-(4-cyanophenyl)urea

Product 1

HCID 202057661-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)urea dihydrochloride monohydrateYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3-chloropropyl)-3-(4-cyanophenyl)urea (3.57 g; 15 mmole), 1-[3-(4-chlorophenyl)propyl]piperazine (3.58 g; 15 mmole), triethylamine (1.52 g; 15 mmole), and ethanol (100 ml) was refluxed for 35 hours. The solvent was removed in vacuo and water added to the residue. The product was extracted with ether, dried, and concentrated in vacuo. The resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1) to give the product as a free base (2.8 g; 42% yield). The product was dissolved in ether and precipitated with ethereal hydrochloric acid to provide, after recrystallization from water, the title compound as colorless crystals, m.p. 219°-221° C.

Workup

  1. temperaturewas refluxed for 35 hours
  2. customThe solvent was removed in vacuo and water
  3. additionadded to the residue
  4. extractionThe product was extracted with ether
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1)
  8. customto give the product as a free base (2.8 g; 42% yield)
  9. customprecipitated with ethereal hydrochloric acid
  10. customto provide
  11. customafter recrystallization from water

Sources & evidence

ORD record
ord-51ea9b802cf74ec88bb506b9b02c6bd6
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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