Benzoic Acid → HCID 86712040, compound

HRID 591210Notes

Reaction equation

HRID 591210 reaction equation
Cl.[CH2:2]([N:9]1[CH2:13][CH:12]([CH2:14][CH2:15][CH2:16]Cl)[C:11](=[O:18])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19]([OH:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C=O)C>[CH2:2]([N:9]1[CH2:13][CH:12]([CH2:14][CH2:15][CH2:16][O:27][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11](=[O:18])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 86712041HCID 86712041, compound

Product 1

HCID 86712040HCID 86712040, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-benzyl-4-(3-chloropropyl)-3-pyrrolidone hydrochloride (6-2, 5.0 g, 17.3 mmol), benzoic acid (2.5 g, 20.8 mmol), potassium carbonate (7.1 g, 51.9 mmol) and potassium iodide (1.4 g, 8.65 mmol) are added to 40 ml DMF, then heated up to 100° C. and finally reacted overnight. At the end of reaction, the temperature is lowered to room temperature, 100 ml water is added, extraction is carried out by ethyl acetate (100 ml×2), organic phase is combined, washed twice by saturated saline water and dried by anhydrous sodium sulfate, and the solvent is dried by concentration under reduced pressure to obtain oily product, which is then purified by column chromatography to obtain oily product (3-1, 2.4 g, 7.1 mmol, yield: 41.1%). 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.1 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.44 (t, J=7.7 Hz, 2H), 7.38-7.27 (m, 5H), 4.32 (t, J=6.3 Hz, 2H), 3.70 (s, 2H), 3.37-3.21 (m, 2H), 2.76 (d, J=17.2 Hz, 1H), 2.50 (dd, J=13.4, 8.0 Hz, 1H), 2.41 (t, J=8.9 Hz, 1H), 1.98-1.71 (m, 3H), 1.54 (m, 1H).

Workup

  1. customAt the end of reaction
  2. customis lowered to room temperature
  3. extractionextraction
  4. washwashed twice by saturated saline water
  5. dry with materialdried by anhydrous sodium sulfate
  6. customthe solvent is dried by concentration under reduced pressure
  7. customto obtain oily product, which
  8. customis then purified by column chromatography
  9. customto obtain oily product (3-1, 2.4 g, 7.1 mmol, yield: 41.1%)

Sources & evidence

ORD record
ord-8ac3033878ed42489b9e7e2ac83e4734
Source dataset
uspto-grants-2016_01
Patent number
US09238648B2

Reaction notes

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