Cyclohexyl isocyanate → HCID 13606713, compound

HRID 543166Notes

Reaction equation

HRID 543166 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]([F: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>C(Cl)Cl>[F: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 20205765HCID 20205765, compound

Product 1

HCID 13606713HCID 13606713, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-fluorobenzyl)-piperazine (2.0 g; 8 mmole) and cyclohexyl isocyanate (1.0 g; 8 mmole) in methylene chloride (20 ml) was stirred overnight at room temperature. The reaction mixture was evaporated, and the residue was mixed with ether (20 ml). The ether solution was filtered, and the filtrate was applied to a silica gel column (300 g) and developed in the same solvent. Fractions containing the product were eluted with methylene chloride/methanol/ammonium hydroxide (45:5:1), and on evaporation provided 1-{3-[4-(4-fluorobenzyl)-piperazin-1-yl]propyl}-3-cyclohexylurea as a pale yellow oil (2.6 g; 85% yield). The product was dissolved in ether, precipitated with ethereal hydrogen chloride and recrystallized from ethanol to yield the title compound as colorless crystals (2.96 g; 80% yield), m.p. 203°-206° C.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was mixed with ether (20 ml)
  3. filtrationThe ether solution was filtered
  4. additionFractions containing the product
  5. washwere eluted with methylene chloride/methanol/ammonium hydroxide (45:5:1)
  6. customon evaporation

Sources & evidence

ORD record
ord-389ba97aac7847069f7cadc1c97eb425
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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