Reaktion #1507856

Reaktionsgleichung

Potassium carbonate

1-ethyl-1-methyl-4-oxo-piperidinium iodide

(R)-1,2,3,4-Tetrahydro-1-naphthylamine

→

(R)-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-one

Lösungsmittel

water

Water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturthe mixture was refluxed for 1 h
3. 3
   Sonstigeethanol was removed in vacuo
4. 4
   Extraktionthe residue was extracted with ethyl acetate
5. 5
   Trocknendried with sodium sulfate
6. 6
   Einengenconcentrated

Vorschrift

(R)-1,2,3,4-Tetrahydro-1-naphthylamine (16 mmol) was dissolved in ethanol (30 ml). Potassium carbonate (9.3 mmol) and 1-ethyl-1-methyl-4-oxo-piperidinium iodide (23 mmol) dissolved in water (30 ml) were added and the mixture was refluxed for 1 h. Water was added, ethanol was removed in vacuo and the residue was extracted with ethyl acetate. Organic phases were pooled, dried with sodium sulfate and concentrated. Chromatography on silica gel (ethyl acetate) yielded (R)-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-one which was dissolved in acetic acid (11 ml). Aniline (14 mmol) and trimethylsilylcyanide (13 mmol) were added and the mixture was stirred for 1.5 h at room temperature. The reaction mixture was poured into cold ammonia solution (water/28% ammonia, 70 ml/30 ml). The solution was adjusted to pH 10 and extracted with methylene chloride. Organic phases were pooled, dried with sodium sulfate and concentrated. Crystallization from diethylether yielded the desired product as a solid. 8.1 g (80%) of (R)4-phenylamino-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-carbonitrile, m.p. 152-153° C. and MIS: m/e=332.3 (M+H+).

Quelle