Hydrochloric Acid → HCID 18687507, compound

HRID 1872762Notes

Reaction equation

HRID 1872762 reaction equation
II.[Mg].[CH2:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br-].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][N+:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.Cl.[NH4+].[OH-].[OH-].[Na+]>C(OCC)C.O>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:20]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 7498Benzyl Bromide2×HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 5462224MagnesiumHCID 18687539HCID 18687539, compound

Product 1

HCID 18687507HCID 18687507, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Iodine (crystals) was added to magnesium turnings (8.63 g) in diethyl ether under N2. Benzyl bromide was added and the Grignard reaction was started. Benzyl bromide (60.65 g) in diethyl ether (443 ml) was added dropwise at reflux temperature while stirring, the reaction mixture was refluxed for 1 hour. The Grignard reagens was added dropwise to a suspension of 4-methoxy-1-(phenylmethyl)pyridinium bromide (75 g) in diethyl ether (1200 ml) and the mixture was stirred at RT for 18 hours. The mixture was poured into HCl (12M; 150 ml) and water (600 ml), alkalized with NH4OH and NaOH and extracted with CH2Cl2. The combined organic layers were washed with water, dried, filtered and the solvent was evaporated, yielding 76 g (100%) of (±)-1,2-dihydro-4-methoxy-1,2-bis(phenylmethyl)pyridine (interm 13).

Workup

  1. customthe Grignard reaction
  2. temperatureat reflux temperature
  3. temperaturethe reaction mixture was refluxed for 1 hour
  4. stirringthe mixture was stirred at RT for 18 hours
  5. extractionextracted with CH2Cl2
  6. washThe combined organic layers were washed with water
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2843ecf3f4b24676a65e05b9ecb428e9
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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