Benzyl Bromide → HCID 57682474, compound

HRID 868763Notes

Reaction equation

HRID 868763 reaction equation
[N:1]12[CH2:11][CH2:10][CH2:9][NH:8][CH:7]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]2.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([N:8]1[CH2:9][CH2:10][CH2:11][N:1]2[CH:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-ene

Product 1

HCID 57682474HCID 57682474, compoundYield 127.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 34.0 g (0.2 mol) 1,8-diazabicylo[5.4.0]undecene and 200 mL toluene was mixed with 34.2 g (0.2 mol) benzyl bromide. An insoluble oil formed and then changed to a white solid as the temperature rose to 57° C. over 10 minutes. After 4 hours, the solid was filtered and dried to provide 62.5 g of 8-benzyl-1,8-diazabicyclo[5.4.0]undecane (the 8-benzyl salt of DBU, which was soluble in water). NaBH4 solution (1.58 g, 5.1 mmol, 4.4M NaBH4 in 14M NaOH solution, obtained from Alfa Aesar, Ward Hill, Mass.) was diluted with 10 mL water. Then, 15 mL t-butyl methyl ether (t-BuOMe) was added to the diluted solution, and the resulting mixture was magnetically stirred and cooled to 3° C. To the cooled mixture was added 3.23 g of the 8-benzyl salt of DBU prepared as described above. After 2 hours, the resulting cold mixture was phase split, the resulting aqueous layer was extracted with t-BuOMe, and the resulting t-BuOMe solutions were combined, dried, and stripped to yield 0.86 g of a product (photolatent catalyst mixture). Gas-liquid chromatographic (GLC) analysis of the product indicated that it contained 39 percent 8-benzyl-1,8-diazabicyclo[5.4.0]undecane (GLC area response with a thermal conductivity detector; identified by gas chromatography/mass spectrometry (GC/MS) analysis), 13 percent of N-3-benzylaminopropylazepine (identified by GC/MS and nuclear magnetic resonance (NMR) analysis), and 48 percent of what was believed to be N-(3-benzylaminopropyl)azepin-2-one (GC/MS mass of 262).

Workup

  1. customAn insoluble oil formed
  2. waitAfter 4 hours
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-da44af9f1c58408dad8b8b88b6dfe62f
Source dataset
uspto-grants-2015_03
Patent number
US08968869B2

Reaction notes

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