Sodium Hydroxide → HCID 22633667, compound

HRID 2416997Notes

Reaction equation

HRID 2416997 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH:5]3[CH2:10][CH:8]2[CH2:7][CH:6]3[NH:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=2)[C:16]([O:18]CCCC)=[O:17])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)CCC>[CH2:1]1[CH:9]2[CH:4]([CH:5]3[CH2:10][CH:8]2[CH2:7][CH:6]3[NH:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=2)[C:16]([OH:18])=[O:17])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22633655HCID 22633655, compound

Product 1

HCID 22633667HCID 22633667, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

600 mg of butyl 3-[(octahydro-4,7-methanoinden-5-ylamino)methyl]benzoate were dissolved in 1 ml of n-butanol, and 2.1 ml of a 1 N aqueous NaOH solution were added. The mixture was stirred at RT for 18 hours and then at 60° C. for 4 hours. The volatile components were then removed under reduced pressure and residual n-butanol was then distilled off twice, azeotropically, under reduced pressure, using in each case 5 ml of water. The residue was taken up in 5 ml of a 10% strength aqueous HCl solution, the volatile components were removed under reduced pressure, and the water was distilled off azeotropically twice, under reduced pressure, using in each case 5 ml of toluene. Since the product still contained considerable amounts of starting material, it was once more dissolved, in 6 ml of methanol, and admixed with 1 ml of a 2 N aqueous NaOH solution. The mixture was stirred at RT for 3 hours, and a further 5 ml of a 2 N aqueous NaOH solution were then added and the mixture was boiled under reflux for 4 hours. The volatile components were removed under reduced pressure, the residue was taken up in 20 ml of water, and the mixture was adjusted to pH=7 using dilute aqueous HCl solution. The mixture was stirred at RT for 1 hour and the product was filtered off with suction and dried under reduced pressure. This gave 260 mg of a crystalline solid, mp 258-261° C.

Workup

  1. waitat 60° C. for 4 hours
  2. customThe volatile components were then removed under reduced pressure and residual n-butanol
  3. distillationwas then distilled off twice
  4. customthe volatile components were removed under reduced pressure
  5. distillationthe water was distilled off azeotropically twice
  6. dissolutionSince the product still contained considerable amounts of starting material, it was once more dissolved, in 6 ml of methanol
  7. stirringThe mixture was stirred at RT for 3 hours
  8. additiona further 5 ml of a 2 N aqueous NaOH solution were then added
  9. temperatureunder reflux for 4 hours
  10. customThe volatile components were removed under reduced pressure
  11. stirringThe mixture was stirred at RT for 1 hour
  12. filtrationthe product was filtered off with suction
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-3fd636725d834000bcb7bd62f308ce7b
Source dataset
uspto-grants-2004_11
Patent number
US06825231B2

Reaction notes

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