Reaktion #358497

Reaktionsgleichung

3-quinuclidyl chloroformate hydrochloride

N-phenylbenzylamine

→

title compound

(R)-Benzylphenylcarbamic acid 1-azabicyclo[2.2.2]oct-3-yl ester hydrochloride

Lösungsmittel

1,2-DCE

1,2-DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe addition
2. 2
   Temperaturthe mixture was refluxed for three hours
3. 3
   SonstigeThe reaction crude
4. 4
   Temperaturto cool down
5. 5
   workup.DISTILLATIONthe solvent distilled off under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography (SiO2, eluent: CHCl3-methanol 10:1)

Vorschrift

To a suspension of 750 mg (2.58 mmol) of 3-quinuclidyl chloroformate hydrochloride in 20 mL of 1,2-DCE, a solution of 395 mg (2.15 mmol) of N-phenylbenzylamine in 5 mL of 1,2-DCE was added dropwise. Once completed the addition, the mixture was refluxed for three hours. The reaction crude was allowed to cool down and the solvent distilled off under reduced pressure. The residue was purified by column chromatography (SiO2, eluent: CHCl3-methanol 10:1) yielding 720 mg (1.95 mmol) of a hygroscopic foam corresponding to the title compound. IR (KBr, cm−1): 3400-3200, 2700-2300, 1700 cm−1. 1H-RMN (CDCl3): 12.30 (s, 1H), 7.20-6.90 (m, 10H), 5.10 (m, 1H), 4.83 (m, 2H), 3.52 (m, 1H), 3.18 (m, 4H), 2.80 (m, 1H), 2.34 (s, 1H), 1.92 (m, 2H), 1.60 (m, 2H).

Quelle