Benzyl Bromide → HCID 23031217, compound

HRID 1766661Notes

Reaction equation

HRID 1766661 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[C:15]([CH3:24])=[CH:16][C:17]([NH2:23])=[C:18]3[C:22]=2[CH2:21][CH2:20][CH2:19]3)=[CH:11][C:10]=1[I:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:28]([N:23]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:17]1[CH:16]=[C:15]([CH3:24])[C:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([I:27])[CH:11]=2)=[C:22]2[C:18]=1[CH2:19][CH2:20][CH2:21]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23031157HCID 23031157, compound

Product 1

HCID 23031217HCID 23031217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(4-benzyloxy-3-iodophenoxy)-6-methylindan-4-ylamine (3.80 g) in N,N-dimethylformamide (15 mL) were added benzyl bromide (2.30 mL) and potassium carbonate (2.67 g), and the mixture was stirred under an argon atmosphere at room temperature for 2 days. Adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1) to give the title compound (4.50 g).

Workup

  1. extractionAdding water, the reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-1fc8c4eb3b2047e28f2c83a8ab958660
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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