Cycloheptylamine → 3-(cycloheptylamino)propane-1-sulfonic Acid

Cycloheptylamine (3.9 mL, 30 mmol) was added to a solution of 1,3-propane sultone (4.1 g, 33 mmol) in THF (65 mL). The mixture was heated at reflux for 5 hours with a heating mantle. The mixture was cooled to room temperature and the solid was collected by filtration, and then dried in a vacuum oven for 1 hour at 60° C. (6.21 g). The solid material was dissolved in methanol/water (30 mL/3 mL, v/v). The solution was cooled slowly to room temperature, and further cooled with an ice-bath. The solid product was collected by filtration, rinsed with methanol, air-dried for 15 minutes, and further dried in a vacuum oven at 60° C. Compound CK was obtained as small white flakes (5.08 g, 72% yield). m.p. 341-43° C. 1H NMR (500 MHz, D2O) δ 1.21-1.42 (m, 8H), 1.45-1.51 (m, 2H), 1.79-1.89 (m, 4H), 2.76 (7, J=7.3 Hz, 2H), 2.96 (t, J=7.8 Hz, 2H), 3.35 (m, J=4.6 Hz, 1H). 13C NMR (125 MHz, D2O) δ 21.6, 23.3, 27.3, 30.5, 43.6, 48.0, 59.6. FT-IR (KBr) νmax 2924, 1615, 1464, 1243.

1. temperatureThe mixture was heated
2. temperatureat reflux for 5 hours with a heating mantle
3. filtrationthe solid was collected by filtration
4. customdried in a vacuum oven for 1 hour at 60° C. (6.21 g)
5. dissolutionThe solid material was dissolved in methanol/water (30 mL/3 mL, v/v)
6. temperatureThe solution was cooled slowly to room temperature
7. temperaturefurther cooled with an ice-bath
8. filtrationThe solid product was collected by filtration
9. washrinsed with methanol
10. customair-dried for 15 minutes
11. customfurther dried in a vacuum oven at 60° C
12. customCompound CK was obtained as small white flakes (5.08 g, 72% yield)

ORD-Eintrag

ord-8e5fb6ddec9144a494daacf08e5656b4

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08642801B2