Sodium Methoxide → HCID 178511575, compound

HRID 979890Notes

Reaction equation

HRID 979890 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH2:5][CH2:4]1.C[O-].[Na+]>CO>[NH2:2][C@@H:3]1[CH2:4][CH2:5][C@H:6]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178479267HCID 178479267, compound

Product 1

HCID 178511575HCID 178511575, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 630 g of the cis 1-(4-aminocyclohexyl)-2-imidazolidinone monohydrochloride and 155 g of sodium methoxide in 6000 ml of anhydrous methanol is stirred at room temperature under an atmosphere of nitrogen for about 24 hours. The reaction mixture is cooled in an ice bath and the sodium chloride filtered off. The methanol filtrate is concentrated to dryness in vacuo. The residue is dissolved in 1700 ml of dichloromethane with heating. The mixture is cooled in an ice bath and filtered through a hyflo filter; the filter cake is washed with 750 ml of dichloromethane. The dichloromethane filtrate is concentrated to dryness in vacuo. The resulting residue is dried in high vacuum to constant weight to give cis 1-(4-aminocyclohexyl)-2-imidazolidinone, m.p. 121°-3°.

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. filtrationthe sodium chloride filtered off
  3. concentrationThe methanol filtrate is concentrated to dryness in vacuo
  4. dissolutionThe residue is dissolved in 1700 ml of dichloromethane
  5. temperaturewith heating
  6. temperatureThe mixture is cooled in an ice bath
  7. filtrationfiltered through a hyflo
  8. filtrationfilter
  9. washthe filter cake is washed with 750 ml of dichloromethane
  10. concentrationThe dichloromethane filtrate is concentrated to dryness in vacuo
  11. customThe resulting residue is dried in high vacuum to constant weight

Sources & evidence

ORD record
ord-6910f7d6bf6a42568bf13bb4f65f2165
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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