Hydrochloric Acid → HCID 11738001, compound

HRID 1059337Notes

Reaction equation

HRID 1059337 reaction equation
[Mg].CO[CH:4]([O:12]C)[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+].Cl>O1CCCC1>[CH2:14]([N:21]1[CH2:26][CH2:25][C:24]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:12])=[CH:10][CH:9]=2)([OH:27])[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 6883421-Bromo-4-(dimethoxymethyl)benzeneHCID 5462224Magnesium

Product 1

HCID 11738001HCID 11738001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Starting with 0.74 g of magnesium, 6.42 g of 4-bromobenzaldehyde dimethyl acetal and 50 ml of tetrahydrofuran, a Grignard reagent was prepared in a conventional manner. Then it was ice-cooled and 10 ml of a solution of 5.67 ml of 1-benzyl-4-piperidone in tetrahydrofuran was dropped thereinto in such a manner that the bulk temperature did not exceed 20° C. After stirring at room temperature for 1 hour, 50 ml of a saturated aqueous solution of ammonium chloride was added thereto and then 1 N-hydrochloric acid was added until the pH value reached about 2. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure and the tetrahydrofuran was distilled off. To the residue were added anhydrous potassium carbonate and ethyl acetate and the resulting mixture was stirred for 15 minutes. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 4.27 g of the title compound as a slightly yellow solid.

Workup

  1. temperaturecooled
  2. customdid not exceed 20° C
  3. stirringAfter stirring for 1 hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. distillationthe tetrahydrofuran was distilled off
  6. additionTo the residue were added anhydrous potassium carbonate and ethyl acetate
  7. stirringthe resulting mixture was stirred for 15 minutes
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  11. distillationAfter distilling off the solvent under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c4cb1dffb0e74e10b692cdbe14fb5320
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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