Hydrochloric Acid → 3-(4-Piperidinyl)-1,2-benzisoxazole Hydrochloride

HRID 370898Notes

Reaction equation

HRID 370898 reaction equation
C1(OC([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][N:17]=3)[CH2:12][CH2:11]2)=O)C=CC=CC=1.C(O)C.[OH-].[K+].[ClH:30]>CCOCC.O>[ClH:30].[NH:10]1[CH2:11][CH2:12][CH:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][N:17]=2)[CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 13076435Phenyl 4-(1,2-benzoxazol-3-yl)piperidine-1-carboxylate

Product 1

HCID 130764373-(4-Piperidinyl)-1,2-benzisoxazole HydrochlorideYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5.0 g of 4-(1,2-benzisoxazole-3-yl)-1-piperidine carboxylic acid phenyl ester, 100 ml of ethanol, 50 g of (85%) potassium hydroxide and 50 ml of water was heated under reflux, with stirring, under nitrogen for 16 hrs. Most of the ethanol was removed in vacuo and the resultant aqueous suspension was extracted with ether (3×50 ml). The ether extracts were combined, washed with water, dried over anhydrous magnesium sulfate and the ether removed under reduced pressure to give an oil. The oil was dissolved in anhydrous ether and hydrogen chloride was introduced to precipitate a 3.0 g of a hydrochloride salt. Recrystallization from methanol-ether gave 2.0 g (57%) of product as the hydrochloride, mp, 313°-315° (dec.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customMost of the ethanol was removed in vacuo
  4. extractionthe resultant aqueous suspension was extracted with ether (3×50 ml)
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe ether removed under reduced pressure
  8. customto give an oil
  9. customto precipitate a 3.0 g of a hydrochloride salt
  10. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-6ab2a419771347b48e3adf4dca67929b
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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