تفاعل #1507856

معادلة التفاعل

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

المذيبات

water

Water

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةthe mixture was refluxed for 1 h
3. 3
   أخرىethanol was removed in vacuo
4. 4
   استخلاصthe residue was extracted with ethyl acetate
5. 5
   تجفيفdried with sodium sulfate
6. 6
   تركيزconcentrated

الإجراء التجريبي

(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+).

المصدر