Hexyl isocyanate → HCID 13606723, compound

HRID 543182Notes

Reaction equation

HRID 543182 reaction equation
[CH2:1]([N:7]=[C:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:16][CH2:15]1>C(Cl)Cl>[ClH:28].[ClH:28].[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:9])[CH2:19][CH2:18]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 75659Hexyl isocyanateHCID 20205743HCID 20205743, compound

Product 1

HCID 13606723HCID 13606723, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of n-hexyl isocyanate (1.27 g; 10 mmole) in methylene chloride (25 ml) was added to a solution of 1-(3-aminopropyl)-4-(4-chlorophenethyl)piperazine (2.82 g; 10 mmole) in methylene chloride (50 ml). The resulting mixture was refluxed for 6 hours and concentrated in vacuo to give a yellow oil which was chromatographed on silica gel (methylene chloride/methanol/ammonium hydroxide; 45/5/1). Precipitation as the dihydrochloride and recrystallization from ethanol provided the title compound (0.91 g; 19% yield) as colorless crystals, m.p. 230°-233° C.

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. concentrationconcentrated in vacuo
  3. customto give a yellow oil which
  4. customwas chromatographed on silica gel (methylene chloride/methanol/ammonium hydroxide; 45/5/1)
  5. customPrecipitation
  6. customas the dihydrochloride and recrystallization from ethanol

Sources & evidence

ORD record
ord-9c5591a8b88b4225b0d19f38b569d921
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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