Trifluoroacetic acid → HCID 22498402, compound

Temperature

0 °C

To a solution of tert-butyl 1-piperazinecarboxylate (2.5 g. 13.42 mmol) in tetrahydrofuran (21.5 ml, 0.25 M) at 0° C. was added triethylamine (2.25 mL, 16.11 mmol) followed by dimethylsulfamoyl chloride (1.73 mL, 16.11 mmol). The reaction mixture was stirred at 0° C. for 1 hour, diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 solution (2×30 mL), followed by brine (2×30 mL). The dried (Na2SO4) organic layer was evaporated to dryness under reduced pressure and the residue obtained was treated with 10% trifluoroacetic acid in methylene chloride (20 mL) at ambient temperature. After 48 hours, methylene chloride was evaporated in vacuo to obtain a colorless syrup. This crude material was made basic (1 N NaOH, 50 mL), and the mixture was extracted sequentially with ethyl acetate (2×20 mL) and methylene chloride (2×30 mL). The combined organic layers were dried (Na2SO4) and evaporated to dryness under reduced pressure to obtain the title compound in quantitative yield. 1H NMR (300 MHz, DMSO-d6) δ 2.77 (s, 3H), 2.79 (s, 3H), 3.12-3.20 (m, 7H), 3.3 (m,1H), 8.86 (br s, 1H); MS (ESI) m/e 194 (M+H)+.

1. washwashed with saturated NaHCO3 solution (2×30 mL)
2. dry with materialThe dried (Na2SO4) organic layer
3. customwas evaporated to dryness under reduced pressure
4. customthe residue obtained
5. waitAfter 48 hours
6. custommethylene chloride was evaporated in vacuo
7. customto obtain a colorless syrup
8. extractionthe mixture was extracted sequentially with ethyl acetate (2×20 mL) and methylene chloride (2×30 mL)
9. dry with materialThe combined organic layers were dried (Na2SO4)
10. customevaporated to dryness under reduced pressure

ORD record

ord-300565a8c62841308a64956902213652

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878700B1