Pyrrolidine → HCID 58790415, compound

HRID 2193756Notes

Reaction equation

HRID 2193756 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([I:10])[N:7]=[CH:6]1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>CS(C)=O.O>[I:10][C:8]1[N:7]=[CH:6][N:5]([CH2:4][CH2:3][CH2:2][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:9]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 58790361HCID 58790361, compound

Product 1

HCID 58790415HCID 58790415, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of the chloride 292 (1.2 g, 4.44 mmol) and pyrrolidine (1.1 mL, 13.3 mmol) in dry DMSO (2 mL) was heated at 60° C. under nitrogen for 3 h. The reaction mixture was cooled, diluted with water and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent methanol-dichloromethane, 5:95 to 20:80) to afford 293 (1.06 g, 3.47 mmol, 78% yield) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.59 (d, J=1.2 Hz, 1H), 7.39 (d, J=1.2 Hz, 1H), 3.98 (t, J=7.2 Hz, 2H), 2.45-2.33 (m, 4H), 2.29 (t, J=7.2 Hz, 2H), 1.84 (q, J=7.2 Hz, 2H), 1.72-1.62 (m, 4H). MS (m/z): 305.9 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent methanol-dichloromethane, 5:95 to 20:80)

Sources & evidence

ORD record
ord-79153ef73e9f421286fe75107ee46158
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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