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Preparation of antiarrhythmic compounds. II

P. Šefčovič, K. Babor, V. Kaláč, and L. Dúbravková

Slovak Academy of Sciences, Bratislava

 

Abstract: cf. CA 56, 4872d. Dehydroabietinol (28.7 g.) in 100 ml. HOAc oxidized with 10 g. K2Cr2O7 in 50 ml. HOAc at 85-94° 2.5 hrs., treated with 500 ml. water, and extd. with Et2O gave 19.4 g. dehydroabietinal (I), m. 87-8° (MeOH), [α]21D 67.5° (EtOH); semicarbazone m. 225-6°. I (71.1 g.) in 200 ml. EtOAc treated with 8.7 g. Na at 30-5°. After reaction, dil. HOAc was added and the mixt. extd. with Et2O. The evapd. ext. was dissolved in a mixt. of 500 ml. EtOH, 160 g. NaOH, and 500 ml. water, the soln. was refluxed 4 hrs. and filtered; from the acidified filtrate, 28 g. 3-(1,12-dimethyl-7-isopropyl-1,2,3,4,9,10,11,12-octahydro-1-phenan threnyl)acrylic acid (II), m. 164-5° (EtOH), [α]21D 77.5° (EtOH), was obtained. II esters prepd. were (b.p. base/mm., m.p. hydrochloride, [α]21D hydrochloride, and % yield base given): 2-dimethylaminoethyl, 220°/0.2, 152°, 60°, 65.8; 2-diethylaminoethyl, 238°/0.15, 145°, 55°, 68.75; 2-piperidinoethyl, 256°/0.2, 141°, 52.7°, 65.65; 2-morpholinoethyl, 277°/0.3, 149°, 51.3°, 63.95. Other esters prepd. were (b.p./ mm., [α]21D and % yield given): of phytenic acid (CA 34, 54377): dimethylaminoethyl, 168-8°/0.15, 0, 56.8; of 9-oxodehydroabietic acid: dimethylaminomethyl, 212°/0.3, -36.8°, 78.2; diethylaminomethyl, 218°/0.2, -37.5°, 82.1; 2-piperidinoethyl, 226°/0.3, -37.6°; 81.3; 2-morpholinoethyl, 233°/0.2, -37.5°, 79.3; of 6-aminodehydroabietic acid: dimethylaminoethyl, 238°/ 0.15, 62.5°, 76.8; 2-diethylaminoethyl, 246°/0.2, 60°, 78.5; 2piperidinoethyl, 225°/0.1, 57.5°, 75.6; 2-morpholinoethyl, 270°/0.15, 52.5°, 73.7.

Full paper in Portable Document Format: 1510a725.pdf (in Slovak)

 

Chemical Papers 15 (10) 725–729 (1961)

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