Reaktion #326937

Reaktionsgleichung

1-ethynylcyclohexylamine

1,3-propane sultone

→

3-(1-ethynylcyclohexyl)amino-1-propanesulfonic acid

Ausbeute 75.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 2 hours (thick paste)
3. 3
   FiltrationThe solid was collected by filtration
4. 4
   Waschenrinsed with THF (3×5 mL)
5. 5
   Sonstigeair-dried 15 minutes (7.3 g)
6. 6
   Temperaturthe suspension was heated
7. 7
   Temperaturat reflux for 1 hour
8. 8
   TemperaturThe mixture was then cooled to room temperature
9. 9
   Filtrationthe solid was collected by suction filtration
10. 10
    Waschenrinsed with ethanol (2×5 mL)
11. 11
    Sonstigeair-dried for 10 min
12. 12
    Sonstigefurther dried in a vacuum oven at 60° C. overnight (crop1, 7.10 g)
13. 13
    FiltrationThe solid was collected by filtration
14. 14
    Waschenrinsed with acetone (3×5 mL)
15. 15
    Sonstigeair-dried for 30 minutes
16. 16
    TemperaturThe suspension was heated
17. 17
    Temperaturat reflux for 1 hour
18. 18
    TemperaturThe mixture was then cooled to room temperature
19. 19
    Filtrationthe solid was collected by suction filtration
20. 20
    Waschenrinsed with ethanol (2×5 mL)
21. 21
    Sonstigeair-dried for 2 minutes
22. 22
    Sonstigefurther dried in a vacuum oven at 60° C. overnight (crop 2: 1.85 g)
23. 23
    SonstigeCompound DX was obtained as a fine white solid (two crops in total 8.95 g, 75% yield)

Vorschrift

A mixture of 1-ethynylcyclohexylamine (6 g, 48.7 mmol) and 1,3-propane sultone (6.55 g, 53.6 mmol) in THF (35 mL) was heated at reflux for 2 hours (thick paste). The mixture was cooled to room temperature. The solid was collected by filtration, rinsed with THF (3×5 mL), air-dried 15 minutes (7.3 g). The solid was suspended in ethanol (30 mL) and the suspension was heated at reflux for 1 hour. The mixture was then cooled to room temperature and the solid was collected by suction filtration, rinsed with ethanol (2×5 mL), air-dried for 10 min, and further dried in a vacuum oven at 60° C. overnight (crop1, 7.10 g). The combined mother liquors were stirred overnight at room temperature. There was a lot of solid. The solid was collected by filtration, rinsed with acetone (3×5 mL), air-dried for 30 minutes, and then suspended in ethanol (12 mL). The suspension was heated at reflux for 1 hour. The mixture was then cooled to room temperature and the solid was collected by suction filtration, rinsed with ethanol (2×5 mL), air-dried for 2 minutes, and further dried in a vacuum oven at 60° C. overnight (crop 2: 1.85 g). Compound DX was obtained as a fine white solid (two crops in total 8.95 g, 75% yield). 1H NMR (500 MHz, D2O) δ 0.95-1.05 (m, 1H), 1.38-1.54 (m, 5H), 1.60-1.64 (m, 2H), 1.94 (qt, J=7.8 Hz, 2H), 2.85 (t, J=7.3 Hz, 2H), 3.01 (s, 1H), 3.22 (t, J=7.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 21.8, 22.3, 24.2, 34.4, 40.9, 48.0, 59.2, 78.6, 79.3. ES-MS 243.0 (M−1).

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