Hydrochloric Acid → HCID 66590945, compound

HRID 1261440Notes

Reaction equation

HRID 1261440 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH2:15])=[CH:9][C:8]=1[O:16][CH3:17].C([O-])([O-])=O.[K+].[K+].[I-].[K+].[CH3:29][O:30][C:31](=[O:34])[CH2:32]Br.[ClH:35]>CN(C)C=O.C(OCC)(=O)C>[ClH:35].[CH3:29][O:30][C:31](=[O:34])[CH2:32][NH:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=2)=[C:8]([O:16][CH3:17])[CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59596817HCID 59596817, compound

Product 1

HCID 66590945HCID 66590945, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g (3.2 mmol) of 2-[4-(3-fluoro-benzyloxy)-3-methoxy-phenyl]-ethylamine, 833 mg (6 mmol) of K2CO3, 50 mg of potassium iodide and 0.27 ml (2.9 mmol) of bromo-acetic acid methyl ester were dissolved in 10 ml of dimethylformamide and the mixture was stirred at room temperature overnight. Solvent was removed, water was added to the residue and the residue was extracted with ethyl acetate. The crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2.5:0.25 gradient v:v:v). The product obtained was dissolved in anhydrous hydrochloric acid in ethyl acetate. The solvent was removed and the residue was triturated with diethyl ether. 482 mg (39% yield) of the title compound were obtained as a brown solid.

Workup

  1. customSolvent was removed
  2. additionwater was added to the residue
  3. extractionthe residue was extracted with ethyl acetate
  4. customThe crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2.5:0.25 gradient v:v:v)
  5. customThe product obtained
  6. customThe solvent was removed
  7. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2d6e76b995ce428eb45252a334631bfc
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

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