تفاعل #529321

معادلة التفاعل

3-aminoacrolein

triethylamine

1,1,3,3-tetramethoxypropane

3-aminoacrolein

cyclohexanone

3-aminoacrolein

→

title compound

المردود 35.0%

5,6,7,8-Tetrahydroquinoline

المردود 35.0%

3-Methoxyacrolein

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture heated in an oil bath at 120° for 24 hours
2. 2
   أخرىThe cooled reaction mixture
3. 3
   غسيلwashed with water and 2N HCl (2 × 20 ml.)
4. 4
   استخلاصextracted with ether
5. 5
   أخرىThe combined extracts were dried
6. 6
   أخرىevaporated
7. 7
   workup.DISTILLATIONthe residue distilled

الإجراء التجريبي

3-Methoxyacrolein was prepared from 1,1,3,3-tetramethoxypropane (Helv. Chim. Acta 1959, 42, 851) and converted to 3-aminoacrolein according to the method of Brietmaier and Gasenmann (Chem. Ber. 1971, 104, 665-7). 5,6,7,8-Tetrahydroquinoline was prepared from 3-aminoacrolein as described by Brietmaier and Bayer (Tet. Letts 1970, 38, 3291). A mixture of 3-aminoacrolein (7.3 gm, 0.1 m) and cyclohexanone (12 gm., 0.12m) was treated with triethylamine (5 ml.) and piperidinium acetate (0.1 gr) and the mixture heated in an oil bath at 120° for 24 hours. The cooled reaction mixture was dissolved in ether (100 ml.), washed with water and 2N HCl (2 × 20 ml.) and the acid washings combined, made basic with sodium carbonate and extracted with ether. The combined extracts were dried, evaporated and the residue distilled to give the title compound as a pale yellow oil (4.5 gm, 35%) b.p. 100°/15 mm.

المصدر