Benzyl Bromide → HCID 11023142, compound

HRID 1057659Notes

Reaction equation

HRID 1057659 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:10](=[O:18])[CH2:11][CH2:12][CH2:13][C:14]=3[NH:15]2)=[CH:7][CH:6]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:15]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:18])[C:9]=2[C:8]2[C:16]1=[CH:17][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11413257HCID 11413257, compound

Product 1

HCID 11023142HCID 11023142, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (0.26 g, 11 mmol) in dry DMF (50 mL) is added 7-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (2.2 g, 10.2 mmol). The mixture is stirred at room temperature for 30 min. To this is added benzyl bromide (1.3 mL, 11 mmol). The mixture is stirred at room temperature overnight. The mixture is partitioned between water and Et2O. The layers are separated and the organic layer washed twice with water (200 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (200 mL) silica gel using CH3OH/CH2Cl2 (2/98) gave 1.7 g (55%) of the title compound; IR (drift) 1638, 1628, 1578, 1535, 1497, 1461, 1449, 1357, 1266, 1200, 1149, 1105, 834, 807, 700 cm−1. 1H NMR (CDCl3) δ2.2, 2.6, 2.8, 3.8, 6.7, 6.9, 7.0, 7.3, 8.1; Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.29; H, 6.39; N, 4.53.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customThe mixture is partitioned between water and Et2O
  3. customThe layers are separated
  4. washthe organic layer washed twice with water (200 mL)
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db62b257855e4dbbba111fd2ff6643fc
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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