Hydrochloric Acid → HCID 19045477, compound

HRID 1781428Notes

Reaction equation

HRID 1781428 reaction equation
N1CCCC1.[OH:6][C:7]1[C:8]([C:16](=[O:18])[CH3:17])=[CH:9][C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1.[C:19]1([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[ClH:34]>CO.C(O)C>[ClH:34].[C:19]1([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][C:30]3([CH2:17][C:16](=[O:18])[C:8]4[CH:9]=[C:10]5[O:14][CH2:13][O:12][C:11]5=[CH:15][C:7]=4[O:6]3)[CH2:29][CH2:28]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 96437N-Phenethyl-4-piperidinoneHCID 11745219Ethanone, 1-(6-hydroxy-1,3-benzodioxol-5-yl)-

Product 1

HCID 19045477HCID 19045477, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

Pyrrolidine (83 ml, 71 mg, 1 mmol) was added to a mixture of 1-(6-hydroxy-1,3-benzodioxol-5-yl)-ethanone [prepared as described by K. Fukui and M. Nakayama, Bull. Chem: Soc. Jap., 1963, 37, 300.] (180 mg, 1 mmol) in methanol (1 ml). The mixture was stirred for 10 minutes, then 1-(2-phenylethyl)-4-piperidinone (203 mg, 1 mmol) in methanol (1 ml) was added and the mixture was heated under reflux for 1.5 hours. The mixture was cooled, the solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 20 ml) was added. The mixture was extracted with dichloromethane (3×20 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (98:2:0.2) to give a yellow glass which was suspended in ethanol (5 ml) and treated with ethanolic HCl (6N, 0.5 ml). The mixture was stirred for 1 hour, cooled and the precipitate was collected and dried in vacuo to give the title compound as a white solid (153 mg, 38%), m.p.>285° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 20 ml)
  5. additionwas added
  6. extractionThe mixture was extracted with dichloromethane (3×20 ml)
  7. dry with materialthe combined organic fractions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (98:2:0.2)
  11. customto give a yellow glass which
  12. stirringThe mixture was stirred for 1 hour
  13. temperaturecooled
  14. customthe precipitate was collected
  15. customdried in vacuo

Sources & evidence

ORD record
ord-4ffa9ca4431d46dc85f632b388fbb1f5
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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