1-Methylpyrrolidine → HCID 67407837, compound

Temperature

180 °C

A mixture of N-(4-amino-2,6-diisopropyl-phenyl)-4-methyl-benzenesulfonamide (346 mg), bis-(2-bromoethyl)ether (151 μL), N,N-diisopropyl-ethylamine (0.53 mL) and N-methylpyrrolidine (1.0 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL) and dried over sodium sulfate. The organic phase was concentrated in vacuo and redissolved in a mixture of sulfuric acid (1.9 mL) and water (0.1 mL) and stirred at 40° C. for 3 hours. Ice (30 mL) and water (30 mL) were added and the mixture was basified with solid potassium carbonate. The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic phases were dried over sodium sulfate and concentrated in vacuo to furnish 260 mg (99%) of the title compound as a white solid. 1H NMR (500 MHz, CDCl3): 1.26 (d, 12H), 2.95 (m, 2H), 3.06 (m, 4H), 3.49 (b, 2H), 3.87 (m, 4H), 6.69 (s, 2H).

1. washwashed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL)
2. dry with materialdried over sodium sulfate
3. concentrationThe organic phase was concentrated in vacuo
4. dissolutionredissolved in a mixture of sulfuric acid (1.9 mL) and water (0.1 mL)
5. additionIce (30 mL) and water (30 mL) were added
6. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
7. dry with materialthe combined organic phases were dried over sodium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-1bcb9e4423d34fa0b69962431bccb5b7

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501414B2