Hydrochloric Acid → HCID 23368417, compound

HRID 1901648Notes

Reaction equation

HRID 1901648 reaction equation
N[CH:2]([CH2:15][CH2:16][CH3:17])[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1.[CH2:18]=O.[C:20]([BH3-])#[N:21].[Na+].Cl.[OH-].[Na+]>CO.C(OCC)(=O)C>[ClH:14].[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][N:6]=[C:5]([O:4][CH2:3][CH:2]([N:21]([CH3:20])[CH3:18])[CH2:15][CH2:16][CH3:17])[C:9]=2[CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23368525HCID 23368525, compound

Product 1

HCID 23368417HCID 23368417, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g of 3-(2-aminopentyloxy)-5-chloro-1,2-benzoisoxazole in 5 ml of methanol is added 5 ml of 37% formalin, and then, 0.16 g of sodium cyanoborohydride is added with ice-cooling, and they are subjected to reaction at room temperature for 24 hours, after which 2N hydrochloric acid is added to adjust the pH to 1.5 and then stirring is effected for a further 30 minutes. Ethyl acetate is added to the reaction mixture, and the pH is adjusted to 9.5 with a 10% (w/w) aqueous sodium hydroxide solution, after which the organic layer is separated. The organic layer separated is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:chloroform:methanol=20:1] and thereafter this is dissolved in ethyl acetate. Thereto is added 5 ml of a dioxane solution (2.2N) of hydrogen chloride, and the crystals precipitated are collected by filtration, to obtain 0.17 g of colorless, crystalline 5-chloro-3-(2-dimethylaminopentyloxy)-1,2-benzoisoxazole hydrochloride having a melting point of 137.1°-137.7° C.

Workup

  1. temperaturecooling
  2. customthey are subjected to reaction at room temperature for 24 hours
  3. customafter which the organic layer is separated
  4. customThe organic layer separated
  5. washis washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent is removed by distillation under reduced pressure
  8. customThe residue obtained
  9. customis purified by a column chromatography [eluant:chloroform:methanol=20:1]
  10. dissolutionthis is dissolved in ethyl acetate
  11. additionThereto is added 5 ml of a dioxane solution (2.2N) of hydrogen chloride
  12. customthe crystals precipitated
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-9ed06178726644fbac27a94f0bd92753
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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