Benzyl Bromide → HCID 19107056, compound

HRID 1197548Notes

Reaction equation

HRID 1197548 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][NH:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][N:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 19106989HCID 19106989, compound

Product 1

HCID 19107056HCID 19107056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

The amine (7.0 g, 23 mmol) from Example 102 and sodium carbonate (4.88 g, 46 mmol) were slurried in ethanol (50 ml). Benzyl bromide was added and the reaction was stirred for 18 hours at 25° C. The reaction was filtered and concentrated. The residue was partitioned between water and dichloromethane. The dichloromethane layer was dried (MgSO4), filtered, and concentrated to yield a crude yellow residue which was chromatographed on a silica gel column eluted initially with dichloromethane followed by methanol/dichloromethane (1:99). The title compound was eluted as a pale yellow oil (7.2 g, 88%).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and dichloromethane
  4. dry with materialThe dichloromethane layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude yellow residue which
  8. customwas chromatographed on a silica gel column
  9. washeluted initially with dichloromethane
  10. washThe title compound was eluted as a pale yellow oil (7.2 g, 88%)

Sources & evidence

ORD record
ord-4e6614d3164342b0bdef4335856277fd
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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