Cyclohexylisopropylamine → HCID 19754886, compound

HRID 1588917Notes

Reaction equation

HRID 1588917 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH:11]([NH:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:13])[CH3:12]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:11]([CH3:13])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 62386CyclohexylisopropylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 19754886HCID 19754886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred, cold (0° C.) solution of 4-bromobenzoyl chloride (5.305 g, 24.2 mmol) in tetrahydrofuran (20 ml) was added dropwise a solution of isopropyl cylcohexyl amine (6.841 g, 48.4 mmol) in tetrahydrofuran (THF) (7ml). After stirring for 1 hr at 0° C., the reaction was stirred at room temperature for 3 hr. and reflexed for 3 hr. The reaction was concentrated in vacuo and the residual mass was dissolved in ethyl ether and water. The layers were separated and the organic layer washed once with water, twice with 0.5N HCl, once more with water, twice with 5% aqueous NaHCO3 solution, and once with water. After drying over sodium sulfate, the organic layer was filtered, and the filtrate concentrated in vacuo to give the crude product. This material was purified by chromatography on silica el suing mixtures of EtOAc, and hexane as eluents to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature for 3 hr
  2. waitand reflexed for 3 hr
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionthe residual mass was dissolved in ethyl ether
  5. customThe layers were separated
  6. washthe organic layer washed once with water, twice with 0.5N HCl, once more with water, twice with 5% aqueous NaHCO3 solution
  7. dry with materialAfter drying over sodium sulfate
  8. filtrationthe organic layer was filtered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give the crude product
  11. customThis material was purified by chromatography on silica el

Sources & evidence

ORD record
ord-8b58b5420ff04bfb9fc7feedd672d4dd
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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