Benzyl Bromide → HCID 135999902, compound

HRID 1986896Notes

Reaction equation

HRID 1986896 reaction equation
[CH3:1][C:2]1[NH:3][N:4]=[C:5]2[C:14]3[CH:13]=[C:12]4[CH2:15][CH2:16][CH2:17][CH2:18][C:11]4=[CH:10][C:9]=3[NH:8][C:7](=[O:19])[C:6]=12.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:3]1[C:2]([CH3:1])=[C:6]2[C:7](=[O:19])[NH:8][C:9]3[CH:10]=[C:11]4[CH2:18][CH2:17][CH2:16][CH2:15][C:12]4=[CH:13][C:14]=3[C:5]2=[N:4]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135999903HCID 135999903, compound

Product 1

HCID 135999902HCID 135999902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-6) (10.2 g, 40.3 mmol, 1 equiv) and potassium carbonate (30.0 g, 217 mmol, 5.38 equiv) in DMF (100 mL) under nitrogen was added benzyl bromide (35.0 g, 205 mmol, 5.09 equiv) and the resulting mixture was stirred at 23° C. for 16 h. The reaction mixture was filtered and the filtered solid was washed with ether (3×200 mL) followed by water (3×250 mL) and dried to yield 2-benzyl-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-7) as a white solid. LRMS m/z (M+H) 344.2 found, 344.2 required.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtered solid was washed with ether (3×200 mL)
  3. customdried

Sources & evidence

ORD record
ord-71b9d3e396f34f0896691ec4205dc768
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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