Cyclohexanone → 1-(4-Chloro-1-butyl)-3-cyclohexyl-2-imidazolidinone

HRID 1057663Notes

Reaction equation

HRID 1057663 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11].[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[BH4-].[Na+]>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:7]1=[O:11]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 4311764Sodium borohydrideHCID 150064221-(4-Chloro-1-butyl)-2-imidazolidinone

Product 1

HCID 186721001-(4-Chloro-1-butyl)-3-cyclohexyl-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(4-chloro-1-butyl)-2-imidazolidinone (50 g) and cyclohexanone (83.3 g) in glacial acetic acid (1000 ml) was stirred for one hour at room temperature. The mixture was cooled to 10-15° C. and NaBH4 (42.4 g) was added in small portions during 5 hours. After stirring overnight at room temperature, acetic acid was evaporated in vacuo. Water (500 ml) and dichloromethane (300 ml) were added and pH adjusted to >9 by addition of aqueous diluted NH4OH. The organic phase was separated, dried with anhydrous MgSO4, filtered and the solvent evaporated in vacuo. The remaining crude product was purified by column chromatography on silica gel (eluted with ethyl acetate). The pure title compound 1a crystalized upon standing. Yield: 33 g, mp: 30-35° C.

Workup

  1. temperatureThe mixture was cooled to 10-15° C.
  2. stirringAfter stirring overnight at room temperature
  3. customacetic acid was evaporated in vacuo
  4. additionWater (500 ml) and dichloromethane (300 ml) were added
  5. additionpH adjusted to >9 by addition of aqueous diluted NH4OH
  6. customThe organic phase was separated
  7. dry with materialdried with anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo
  10. customThe remaining crude product was purified by column chromatography on silica gel (eluted with ethyl acetate)
  11. customThe pure title compound 1a crystalized

Sources & evidence

ORD record
ord-e6d93097e19f457e9e25ce9463057003
Source dataset
uspto-grants-2003_02
Patent number
US06514993B1

Reaction notes

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