Hydrochloric Acid → 1-(5-Phenyl-4,5-dihydroisoxazol-3-ylmethyl)-4-(4-chlorophenyl)-4-hydroxypiperidine hydrochloride

HRID 434519Notes

Reaction equation

HRID 434519 reaction equation
[Cl:1][CH2:2][C:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([OH:27])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OC(C)C)(C)C.C(O)C>[ClH:1].[C:8]1([CH:6]2[O:5][N:4]=[C:3]([CH2:2][N:24]3[CH2:23][CH2:22][C:21]([C:18]4[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=4)([OH:27])[CH2:26][CH2:25]3)[CH2:7]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 114582493-(Chloromethyl)-5-phenyl-4,5-dihydro-1,2-oxazole

Product 1

HCID 204928221-(5-Phenyl-4,5-dihydroisoxazol-3-ylmethyl)-4-(4-chlorophenyl)-4-hydroxypiperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

3-Chloromethyl-5-phenyl-4,5-dihydroisoxazole (5.87 g), 6.3 g of 4-(4-chlorophenyl)-4-hydroxypiperidine, 4 g of potassium carbonate and 50 ml of ethanol are heated to 60°-70° C. with stirring for 6 hours. The reaction mixture is filtered and the filtrate is condensed by distillation under reduced pressure. To the residue are added 200 ml of ethyl acetate and 100 ml of water. The organic layer is separated off, washed with water, dried on magnesium sulfate and evaporated under reduced pressure. The residue thus obtained is dissolved in isopropyl ether and alcoholic hydrochloric acid is added to the solution. The crystals thus formed are filtered and then recrystallized from isopropyl alcohol, giving 1-(5-phenyl-4,5-dihydroisoxazol-3-ylmethyl)-4-(4-chlorophenyl)-4-hydroxypiperidine hydrochloride. Melting point: 175°-176° C. (decomposition)

Workup

  1. filtrationThe reaction mixture is filtered
  2. customcondensed
  3. distillationby distillation under reduced pressure
  4. additionTo the residue are added 200 ml of ethyl acetate and 100 ml of water
  5. customThe organic layer is separated off
  6. washwashed with water
  7. customdried on magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue thus obtained
  10. customThe crystals thus formed
  11. filtrationare filtered
  12. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-8899a4c4c5234056a750af5002a1a8a4
Source dataset
uspto-grants-1983_08
Patent number
US04397853

Reaction notes

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