Potassium Carbonate → HCID 19611720, compound

HRID 1602575Notes

Reaction equation

HRID 1602575 reaction equation
[CH3:1][CH:2]([NH2:28])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][O:27][C:21]=2[CH:20]=1)[CH2:4][C:5]1[O:6][C:7]([C:10](=[O:18])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1.ClCC1OC(C(=O)NC2C=CC=CC=2)=CC=1.C1OC2C=CC(CC(=O)C)=CC=2O1.[N+](C1C=CC(CC(=O)C)=CC=1)([O-])=O.ClCC1O[C:76]([C:78]([O:80][CH2:81]C)=[O:79])=CC=1.C(=O)([O-])[O-].[K+].[K+].BrCC(OC)=O>CN(C)C=O.O>[CH3:81][O:80][C:78]([CH2:76][NH:28][CH:2]([CH3:1])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][O:27][C:21]=2[CH:20]=1)[CH2:4][C:5]1[O:6][C:7]([C:10](=[O:18])[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)=[O:79]

Participants

10

Reactant 7

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 784073,4-Methylenedioxyphenyl-2-propanoneHCID 2193671-(4-Nitrophenyl)propan-2-oneHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 13515708HCID 13515708, compound2×HCID 19611725HCID 19611725, compound

Product 1

HCID 19611720HCID 19611720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

200 mg of N-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine prepared in the same manners as in Reference Example 4(1) to (3) by using 3,4-methylenedioxyphenylacetone and 2-(chloromethyl)-5-phenylcarbamoylfuran prepared in Reference Example 5 instead of 4-nitrophenylacetone and ethyl 5-(chloromethyl)-2-furancarboxylate used as the starting materials in Reference Example 4 was dissolved in 3 ml of dimethylformamide, and 88 mg of potassium carbonate was added. 88 mg of methyl bromoacetate was added under cooling with ice, and the resulting solution was stirred at room temperature for 15 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5717; hexane/ethyl acetate=1/1] to give 159 mg of the title compound as a colorless foamy substance.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5717; hexane/ethyl acetate=1/1]

Sources & evidence

ORD record
ord-8a1487ca691b404985240c75dfd61e94
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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