Cyclohexyl isocyanate → HCID 13606730, compound

HRID 1380190Notes

Reaction equation

HRID 1380190 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:7][CH2:6]1.[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:27]([NH:26][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:28])[CH2:6][CH2:7]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 20205741HCID 20205741, compound

Product 1

HCID 13606730HCID 13606730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)homopiperazine (2.16 g; 7.7 mmole) in methylene chloride (30 ml) was stirred at room temperature with cyclohexyl isocyanate (1.05 g; 8.5 mmole) for one hour. The reaction mixture was concentrated under reduced pressure to an oil which was chromatographed on silica gel (methylene chloride/methanol/ammonium hydroxide: 97/2.5/0.5) to yield 1-{3-[4-(4-chlorobenzyl)homopiperazin-1-yl]propyl}-3-cyclohexylurea as a colorless oil. This oil was dissolved in ether and precipitated with ethereal hydrogen chloride to provide the title compound (2.25 g; 61% yield) as a white crystalline solid, m.p. 167°-175° C. (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to an oil which
  2. customwas chromatographed on silica gel (methylene chloride/methanol/ammonium hydroxide: 97/2.5/0.5)

Sources & evidence

ORD record
ord-474f970f659541bbb85ff5006f3cadfc
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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