Ethanol → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-phenylurea

HRID 1380182Notes

Reaction equation

HRID 1380182 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)C>O1CCCC1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:26]([NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:27])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7672Phenyl isocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 136066781-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-phenylureaYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (2.0 g; 7.5 mmole) and phenyl isocyanate (1.6 g; 13.4 mmole) in tetrahydrofuran (5 ml) was stirred at room temperature for 30 minutes. Ethanol (5 ml) was added, and the reaction mixture was stirred for 3 hours and then concentrated under reduced pressure. The residue was crystallized from aqueous ethanol to provide crude product (2.7 g). Recrystallization from the same solvent yielded the title compound as colorless crystals (0.62 g; 21% yield), m.p. 135°-137° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was crystallized from aqueous ethanol
  3. customto provide crude product (2.7 g)
  4. customRecrystallization from the same solvent

Sources & evidence

ORD record
ord-d61f9f2102da41b6a46ba3319715bac8
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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