Hydrochloric Acid → HCID 67714944, compound

HRID 53234Notes

Reaction equation

HRID 53234 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22](=[O:24])[CH3:23])([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](OC)(=[O:30])[C:26]([O:28]C)=[O:27].[H-].[Na+].Cl>C(COC)OC.C1COCC1>[ClH:21].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22](=[O:24])[CH2:23][C:25](=[O:30])[C:26]([OH:28])=[O:27])([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11120Dimethyl oxalateHCID 24758Sodium hydrideHCID 19962174N-Benzyl-4-Acetyl4-(4-Chlorobenzyl)-piperidine

Product 1

HCID 67714944HCID 67714944, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N-Benzyl-4-Acetyl-4-(4-Chlorobenzyl)-piperidine (600 mg, 1.75 mmol) and dimethyl oxalate (310 mg, 2.63 mmol) in dimethoxyethane (20 mL) was treated with sodium hydride (105 mg of a 60% dispersion in mineral oil, 2.63 mmol) and heated to reflux for 3 hours. The reaction was then cooled to room temperature, poured into 1 N aqueous HCl (200 mL) and extracted with ethyl ether (1×50 mL). The ether extract was discarded. The pH of the aqueous phase was adjusted to pH 8 and extracted with ethyl acetate (3×200 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The crude ester thus obtained was dissolved in THF (5 mL) and 3 N HCl (20 mL) and heated to reflux for 1 hour. The reaction was then cooled to room temperature, and concentrated at reduced pressure. The residue was triturated with tetrahydrofuran and the solid collected by filtration and crystallized from isopropanol to give 200 mg of the title compound. mp. 189°-181° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl ether (1×50 mL)
  4. extractionThe ether extract
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customThe crude ester thus obtained
  10. temperatureto reflux for 1 hour
  11. temperatureThe reaction was then cooled to room temperature
  12. concentrationconcentrated at reduced pressure
  13. customThe residue was triturated with tetrahydrofuran
  14. filtrationthe solid collected by filtration
  15. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-93cb5847f89c45208aab8d85dcdc66e3
Source dataset
uspto-grants-1997_04
Patent number
US05618830

Reaction notes

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