Benzyl Bromide → HCID 12549418, compound

HRID 1808278Notes

Reaction equation

HRID 1808278 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>C1(C)C=CC=CC=1>[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

4

Reactant 2

HCID 7498Benzyl BromideHCID 102854-Methylquinoline

Product 1

HCID 12549418HCID 12549418, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of lepidine (14.3 g, 0.1 mol) in toluene (200 mL), benzyl bromide (34.2 g, 0.2 mol) was added dropwise at room temperature. After the addition, the mixture was heated to reflux for 5 hrs. The mixture was cooled to room temperature; the precipitate formed was collected by filtration, washed with toluene and dried under vacuum to give Compound 5 as yellow solid (18.2 g, 58%). It was used without further purification. The structure of Compound 5 is given below:

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 hrs
  4. customthe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with toluene
  7. customdried under vacuum

Sources & evidence

ORD record
ord-485d6dad28664a6f80837d425be0f6d4
Source dataset
uspto-grants-2013_01
Patent number
US08357801B2

Reaction notes

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