Propylamine → Propyl pentanesulfonamide

Temperature

0 °C

Pentane sulfonyl chloride (687 mg, 4.03 mmol) was dissolved in 5 mL CH2Cl2 and added to an ice-cooled solution of n-propylamine (0.40 mL, 4.82 mmol) and ethyldiisopropylamine (0.85 mL, 4.88 mmol) in 5 mL CH2Cl2 under a nitrogen atmosphere. The reaction was stirred at 0° C. for 30 min, then at 25° C. for 4 h. The solution was partitioned between 20 mL of 1.0 M aqeous NaHSO4 and 25 mL CH2Cl2. The organic phase was washed sequentially with 25 mL H2O and 25 mL brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide 739 mg (3.83 mmol, 95%) of the title compound as a white solid. TLC (25% EtOAc-hexane) Rf 0.23; 1H NMR (CDCl3, 300 MHz) δ 0.92 (t, J=7 Hz, 3H), 0.97 (t, J=7 Hz, 3H), 1.28-1.50 (br m, 4H), 1.52-1.68 (m, 2H), 1.75-1.90 (br m, 2H), 2.98-3.06 (m, 2H), 3.08 (q, J=6 Hz, 2H), 4.10-4.23 (br m, 1H); MS (DCl/NH3) m/e 211 (M+NH4)+.

1. waitat 25° C. for 4 h
2. customThe solution was partitioned between 20 mL of 1.0 M aqeous NaHSO4 and 25 mL CH2Cl2
3. washThe organic phase was washed sequentially with 25 mL H2O and 25 mL brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-9ff45ba4ca86428bb9b0f1bdd5509521

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06946481B1