Cyclohexylisopropylamine → HCID 19754867, compound

HRID 1588936Notes

Reaction equation

HRID 1588936 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[Cl:11].[CH:12]([NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([CH3:14])[CH3:13]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]([CH3:14])[CH3:13])=[O:7])=[CH:4][C:3]=1[Cl:11]

Participants

4

Reactant 2

HCID 62386CyclohexylisopropylamineHCID 197549054-Bromo-3-chlorobenzoyl chloride

Product 1

HCID 19754867HCID 19754867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cold (0° C.) solution of 4-bromo-3-chlorobenzoyl chloride (6.14 g, 24.2 mmol) in tetrahydrofuran (20 ml) is added dropwise a solution of isopropyl cyclohexyl amine (6.841g, 48.4 mmol) in THF (7 mL). After stirring for 1 hr. at 0° C., the reaction is stirred at room temperature for 3 hr. and refluxed for 3 hr. The reaction is concentrated in vacuo and the residual mass is dissolved in ethyl ether and water. The layers are separated and the organic layer washed once with water, twice with 0.5N HCl, once more with water, twice with 5% aqueous NaHO3 solution, and once with water. After drying over sodium sulfate, the organic layer is filtered, and the filtrate concentrated in vacuo to give the crude product. This material is purified by chromatography on silica gel using mixtures of EtOAc, and hexane as eluents to give the title compound.

Workup

  1. stirringat 0° C., the reaction is stirred at room temperature for 3 hr
  2. temperatureand refluxed for 3 hr
  3. concentrationThe reaction is concentrated in vacuo
  4. dissolutionthe residual mass is dissolved in ethyl ether
  5. customThe layers are separated
  6. washthe organic layer washed once with water, twice with 0.5N HCl, once more with water, twice with 5% aqueous NaHO3 solution
  7. dry with materialAfter drying over sodium sulfate
  8. filtrationthe organic layer is filtered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give the crude product
  11. customThis material is purified by chromatography on silica gel using mixtures of EtOAc, and hexane as eluents

Sources & evidence

ORD record
ord-7e3d9b12e4dc47f5b7ad7ffede9e4ccb
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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