Potassium Carbonate → HCID 21349896, compound

HRID 2186750Notes

Reaction equation

HRID 2186750 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([OH:26])[C:20]=2[O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:20]=2[O:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21349882HCID 21349882, compound

Product 1

HCID 21349896HCID 21349896, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-(3-(2-naphthylmethylamino)propyl)-8-hydroxy-3,4-dihydro-2H-1,4-benzoxazine (166 mg) was dissolved in DMF (3 ml), and potassium carbonate (63 mg) and methyl bromoacetate (0.045 ml) were added. to the resultant solution at 0° C., followed by stirring at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=2:3) to obtain the object compound (140 mg, yield 73%).

Workup

  1. customat 0° C.
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=2:3)

Sources & evidence

ORD record
ord-af10500ac92e4fda8cac109ac759391c
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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