Hydrochloric Acid → HCID 68773398, compound

HRID 1174451Notes

Reaction equation

HRID 1174451 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[O:13]1[CH2:18][CH2:17]OCC1.[CH:19]1[C:28]2[C:23](=[CH:24]C=C[CH:27]=2)[CH2:22][CH2:21][C:20]=1N1CCCC1.Cl>CCCCCC.C(OCC)(=O)C>[C:3]1([CH2:2][CH:27]2[C:28]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:24][CH2:17][C:18]2=[O:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidineHCID 1378441-(Bromomethyl)naphthalene

Product 1

HCID 68773398HCID 68773398, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Added to a mixed solution of 30.53 g (124.08 mmol, purity: 90.4%) of 1-(bromomethyl)naphthalene and 180 ml of dehydrated dioxane was 30.27 g (151.89 mmol) of 1-(3,4-dihydronaphthalene-2-yl)pyrrolidine, and the mixture was stirred for 5 hours while heating and refluxing. After cooled down to room temperature, 100 ml of a 5% hydrochloric acid aqueous solution was dropwise added to the reaction mixture and stirred, and the mixture was extracted twice with dichloromethane. The organic phase was dried on anhydrous sodium sulfate and filtered, and then the solvent was removed by distillation. A crude product obtained was refined by column chromatograph (silica gel: hexane/ethyl acetate=10/1) to obtain 20.47 g (purity: 51.8%) of 1-(naphthalene-1-ylmethyl)-3,4-dihydronaphthalene-2(1H)-one.

Workup

  1. temperaturewhile heating
  2. temperaturerefluxing
  3. stirringstirred
  4. extractionthe mixture was extracted twice with dichloromethane
  5. dry with materialThe organic phase was dried on anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by distillation
  8. customA crude product obtained

Sources & evidence

ORD record
ord-96bd0579e1ba4950b3f2395fe350d3ac
Source dataset
uspto-grants-2010_11
Patent number
US07838130B2

Reaction notes

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