Hydrochloric Acid → HCID 18174370, compound

HRID 395330Notes

Reaction equation

HRID 395330 reaction equation
II.[CH2:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][N:12]1[CH2:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH2:14][CH2:13]1.Cl>CCOCC.C(Cl)C1C=CC=CC=1.O>[CH2:3]([CH:15]1[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH:16]1[C:18]([O:20][CH3:21])=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 2230ArecolineHCID 7503Benzyl Chloride3×

Product 1

HCID 18174370HCID 18174370, compound

Reagents, catalysts & solvents 3

HCID 7503Benzyl ChlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent5×

Conditions

Temperature
-15 °C

Procedure

To a solution of 480 mg of Mg in 2 mL of dry ether was added a little bit of I2 and several drops of benzyl chloride (about 0.5 mL) of the solution of 2.3 mL (20 mmol) of benzyl chloride in 10 mL of ether. The mixture was gentle stirred, as soon as the reaction sets in, the reminder of benzyl chloride in ether was added at the rate that the reaction went vigorously by cooling the flask with water. Then the resulting solution was stirred at gentle reflux for fifteen minutes after, all the benzyl chloride has been added. Another 5 mL of dry ether was added to the Grignard reagent solution and it was cooled to −15° C., the arecoline (1.5 g) in 20 mL of dry ether was added dropwise to it. The resulting mixture was stirred at −15° C. for another 0.5 hour. The mixture was cooled to about −40° C. and treated slowly with 10% HCl (22 mL). The aqueous layer was separated, extracted with ether (20 mL), and then basified with saturated sodium bicarbonate solution when cooled in an ice bath. The mixture was extracted with ether and the combined organic extracts were washed with brine, dried and concentrated under reduced pressure. Flash chromatography afforded a mixture of cis isomer 76 and trans isomer 77 (500 mg, 21%).

Workup

  1. additionwas added at the rate that the reaction
  2. additionhas been added
  3. stirringThe resulting mixture was stirred at −15° C. for another 0.5 hour
  4. temperatureThe mixture was cooled to about −40° C.
  5. customThe aqueous layer was separated
  6. extractionextracted with ether (20 mL)
  7. temperaturecooled in an ice bath
  8. extractionThe mixture was extracted with ether
  9. washthe combined organic extracts were washed with brine
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customFlash chromatography afforded
  13. additiona mixture of cis

Sources & evidence

ORD record
ord-b7edc87489af4b42956b80a452cc82ac
Source dataset
uspto-grants-2003_08
Patent number
US06605621B1

Reaction notes

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