Benzyl Bromide → HCID 12549418, compound

HRID 1266952Notes

Reaction equation

HRID 1266952 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[CH2:12]([Br:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C>C(#N)C>[Br-:19].[CH2:12]([N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 102854-Methylquinoline

Product 1

HCID 12549418HCID 12549418, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
93 °C

Procedure

A solution of lepidine (37.82 g) and benzyl bromide (6.471 g) in acetonitrile (100 mL) were stirred and heated to reflux in an oil bath at 93° C. for 20 hours. Cooled the reaction mixture to room temperature, added ethyl acetate (50 mL) and stirred for 30 min. The resultant solid was collected, washed with ethyl acetate (4×20 mL) and dried in the air. The filtrate was concentrated to a small volume and a second crop of solid was also collected. The combined solid was dried in an oven under high vacuum at 50° C. overnight. There was obtained 11.52 g (96.9%) of product.

Workup

  1. temperatureheated
  2. temperatureCooled the reaction mixture to room temperature
  3. customThe resultant solid was collected
  4. washwashed with ethyl acetate (4×20 mL)
  5. customdried in the air
  6. concentrationThe filtrate was concentrated to a small volume
  7. customa second crop of solid was also collected
  8. customThe combined solid was dried in an oven under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-9ecbdb3f488b4bb3ac8fd9366a9f3c3b
Source dataset
uspto-grants-2003_04
Patent number
US06551831B2

Reaction notes

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