Acetic Acid → HCID 14575053, compound

HRID 1723080Notes

Reaction equation

HRID 1723080 reaction equation
Cl.Cl[CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][N:13]=2)[CH:9]=[N:8][CH:7]=1.CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1>[CH:7]1[N:8]=[CH:9][N:10]2[CH:11]([C:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[O:14][N:13]=3)[CH2:3][CH2:4][CH2:5][C:6]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 22165658HCID 22165658, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14575053HCID 14575053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-[(5-(3-chloropropyl)-1H-imidazol-1-yl)methyl]-1,2-benzisoxazole hydrochloride (1.9 g, 0.006 mole) in anhydrous tetrahydrofuran (25 mL) is stirred under an atmosphere of nitrogen and cooled in an ice bath during the portionwise addition of solid potassium t-butoxide (1.7 g, 0.015 mole). The reaction mixture is stirred at 0°-5° C. for 3 hours and then acidified by addition of glacial acetic acid (0.5 mL). The solvent is evaporated and the residue is taken up in methylene chloride (20 mL) and washed with saturated sodium bicarbonate (10 mL) and water (10 mL). The solution is dried over anhydrous sodium sulfate, filtered and evaporated to give crude 3-(5,6,7,8-tetrahydroimidazo-[1,5-a]-pyridin-5-yl)-1,2-benzisoxazole which is converted to the hydrochloride salt, m.p. 250°-252° C., when its solution in isopropanol is treated with ethereal hydrogen chloride.

Workup

  1. stirringThe reaction mixture is stirred at 0°-5° C. for 3 hours
  2. customThe solvent is evaporated
  3. washwashed with saturated sodium bicarbonate (10 mL) and water (10 mL)
  4. dry with materialThe solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4f6c8ecaccec4b4ab41119641feb1f4f
Source dataset
uspto-grants-1989_08
Patent number
US04859691

Reaction notes

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