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

HRID 543169Notes

Reaction equation

HRID 543169 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-ef747fa4c9ae4a4a98e6001073fc3885
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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