Hydrochloric Acid → HCID 10424978, compound

HRID 843264Notes

Reaction equation

HRID 843264 reaction equation
[Mg].II.[Cl:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[Cl:11].[CH3:13][N:14]1[CH2:19][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH2:16][CH2:15]1.Cl>CCOCC>[CH3:13][N:14]1[CH2:15][CH2:16][CH:17]([C:7]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=2)[CH:18]([C:20]([O:22][CH3:23])=[O:21])[CH2:19]1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 807IodineHCID 2230ArecolineHCID 290134-Bromo-1,2-dichlorobenzeneHCID 5462224Magnesium

Product 1

HCID 10424978HCID 10424978, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-20 °C

Procedure

To magnesium (5.5 g, 229 mmol) and a few crystals of iodine in anhydrous ether (20 mL) was added 3,4-dichlorobromobenzene (46.4 g, 206 mmol) in anhydrous ether (200 mL) at a rate sufficient to keep the reaction at reflux. After the addition was completed the reaction was heated at reflux for another 15 min. The reaction was cooled to −20° C. and arecoline (16 g, 103 mmol) in anhydrous ether (200 mL) was added over 20 min while keeping the temperature at −20° C. The reaction was stirred for another 2 hour at −20° C. and then heated to 0° C. Hydrochloric acid (4 N, 80 mL) was added and the pH adjusted to 1 using concentrated hydrochloric acid. The organic phase was separated off and the pH adjusted to 9 with concentrated ammonia. Extraction with ether (2×200 mL)afforded 24.6 g of the title compound as a brownish oil.

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. additionAfter the addition
  4. temperaturewas heated
  5. temperatureat reflux for another 15 min
  6. customat −20° C
  7. temperatureheated to 0° C
  8. customThe organic phase was separated off
  9. extractionExtraction with ether (2×200 mL)

Sources & evidence

ORD record
ord-2254c6726ae145bfa797a0e5d5fac57d
Source dataset
uspto-grants-2002_04
Patent number
US06376673B1

Reaction notes

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