Cyclohexyl isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-cyclohexylurea

HRID 543161Notes

Reaction equation

HRID 543161 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.[CH:19]1([N:25]=[C:26]=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>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][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:27])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 136066681-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-cyclohexylureaYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)-piperazine (2.0 g; 7.5 mmole) and cyclohexyl isocyanate (1.6 g; 12.8 mmole) in tetrahydrofuran (5 ml) was stirred at room temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure, and the residual oil was dissolved in ethanol (10 ml). The crude product was precipitated as a white solid by the addition of water, collected at filtration and recrystallized twice from cyclohexane to yield 1-{3-[4-(4-chlorobenzyl)piperazin-1-yl]-propyl}-3-cyclohexylurea (1.62 g; 56% yield) as a white crystalline solid, m.p. 109°-112° C. This product in methylene chloride (20 ml) was precipitated as the dihydrochloride by the addition of excess anhydrous hydrogen chloride. Recrystallization from water provided the title compound as colorless crystals, m.p. 184°-187° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residual oil was dissolved in ethanol (10 ml)
  3. customThe crude product was precipitated as a white solid by the addition of water
  4. filtrationcollected at filtration
  5. customrecrystallized twice from cyclohexane

Sources & evidence

ORD record
ord-8a0ca059ef9e416c872f44d161b6fae7
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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