Benzyl Bromide → HCID 18671654, compound

HRID 1057601Notes

Reaction equation

HRID 1057601 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]2=1.CCCCC.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(Br)C1C=CC=CC=1>[CH2:23]([N:13]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]=2[C:6]2[C:14]1=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8003PentaneHCID 24758Sodium hydrideHCID 11830419HCID 11830419, compound

Product 1

HCID 18671654HCID 18671654, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 7498Benzyl BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

8-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.1967 g, 0.99 mmol) is added to a slurry of pentane-washed NaH (0.0485 g, 0.0012 mol) in DMF (2 mL) and after stirring for 30 min, benzyl bromide (0.14 mL, 0.0012 mol) is added. After 3 h starting material still remained, so additional benzyl bromide (0.015 mL, 0.013 mmol) is added and the mixture is stirred overnight at room temperature. The mixture is then partitioned between aq. sodium bicarbonate and ethyl acetate and the organic layer is dried over sodium sulfate and concentrated to dryness. The resulting solids are recrystallized from ethyl acetate/hexane/dichloromethane to give 0.2076 g (73%) of the title compound; mp 165-166° C.; MS (ESI+) for C20H19NO m/z 290.2 (M+H)+; IR (drift) 2940, 1637, 1599, 1538, 1494, 1462, 1447, 1416, 1357, 1322, 1121, 787, 752, 727, 697 cm−1; 1H NMR (CDCl3) δ2.21, 2.51, 2.59, 2.82, 5.58, 6.89, 6.95, 7.16, 7.29, 8.23. Anal. Calcd for C20H19NO: C, 83.01; H, 6.62; N, 4.84. Found: C, 82.53; H, 6.62; N, 4.86.

Workup

  1. waitAfter 3 h starting
  2. stirringthe mixture is stirred overnight at room temperature
  3. customThe mixture is then partitioned between aq. sodium bicarbonate and ethyl acetate
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting solids are recrystallized from ethyl acetate/hexane/dichloromethane

Sources & evidence

ORD record
ord-a20f9abc449e4f859c9abc95cfc61565
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

Loading…