N-methyl-2-pyrrolidone → HCID 46178739, compound

HRID 339700Notes

Reaction equation

HRID 339700 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([Br:26])=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([C:17]1[N:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]3=[N:19][N:18]=1)[CH:13]=[CH:12]2)(=O)=O.[CH3:29][CH:30]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]1.CN1C(=O)CCC1>O>[N:19]1[N:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]3[C:16](=[C:7]([N:32]4[CH2:33][CH2:34][CH2:35][CH:30]([CH3:29])[CH2:31]4)[C:8]([Br:26])=[CH:9][CH:10]=3)[N:15]=2)[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=12

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 790813-MethylpiperidineHCID 87319342HCID 87319342, compound

Product 1

HCID 46178739HCID 46178739, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Step G (0.025 g, 0.0528 mmol) and 3-methylpiperidine (0.0186 mL, 0.158 mmol) were added to a small microwave reaction vial followed by NMP (0.250 mL). The vessel was placed inside the center of the microwave oven and then it was exposed to microwave irradiation (250 W) for 20 minutes at a temperature of 195° C. After the irradiation, the reaction mixture was cooled to ambient temperature, poured into 10 mL of water and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed with saturated brine and dried over anhydrous Na2SO4. After removal of the solvent, the residue was purified by column chromatography on silica gel to give the product as a dark orange semisolid which was 80% pure. This material was purified via Preparative TLC using 50% Acetone/hexane as eluent to provide 0.005 g (22%) of the product as an orange film. MS ESI (+) m/z 422.3 (M) detected.

Workup

  1. customit was exposed to microwave irradiation (250 W) for 20 minutes at a temperature of 195° C
  2. customAfter the irradiation
  3. extractionextracted with CH2Cl2 (3×10 mL)
  4. washThe combined organic extracts were washed with saturated brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d90e5ac1c978470c9ebb949e46971e37
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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