Shepard, Edwin R.’s team published research in Journal of Organic Chemistry in 19 | CAS: 18928-94-4

Journal of Organic Chemistry published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C9H8O4, Related Products of bromides-buliding-blocks.

Shepard, Edwin R. published the artcilePapaverine analogs. IV. 1-Cycloalkyl-6,7-dimethoxyisoquinolines, Related Products of bromides-buliding-blocks, the publication is Journal of Organic Chemistry (1954), 415-18, database is CAplus.

cf. C.A. 47, 9970f. A number of 1-cycloalkylisoquinolines related to papaverine have been prepared for pharmacol. evaluation. Reduction of 120 g. Et cyclopentylacetate in 120 cc. ether with 20 g. LiAlH4 in 100 cc. ether gives 82% β-cyclopentylethanol, b23 94-5°, which (72 g.), treated with an excess of anhydrous HBr, gives 99% β-cyclopentylethyl bromide (I), b19 76-8°. Adding 111 g. I to 62 g. NaCN in 125 cc. H2O and 250 cc. Methyl Cellosolve with stirring and refluxing, refluxing the mixture 6 hrs., diluting it with H2O, and extracting with ether give 80% β-cyclopentylpropionitrile, b19 98-100°, nD25 1.4490, which (40 g.), refluxed 12 hrs. with 300 cc. 25% NaOH, gives 92% β-cyclopentylpropionic acid, b14 134-6°. Heating 36.2 g. homoveratrylamine and 22.8 g. cyclopentanecarboxylic acid 1 hr. at 190-200° in an open flask gives 73% N-homoveratrylcyclopentanecarboxamide, m. 95.5-6.5°. Similarly are prepared: N-homoveratrylcyclopentylacetamide, 90%, m. 88-9°; N-homoveratryl-β-cyclopentylpropionamide, 85%, m. 89-90°; N-homoveratrylcyclohexanecarboxamide, 84%, m. 111.5-12.5°; N-homoveratryl-β-cyclohexylpropionamide, 77%, m. 94.5-5.5°. These amides are converted into the following 1-cycloalkyl-6,7-dimethoxyisoquinolines-HCl according to the method described earlier: 1-cyclopentyl, 64%, m. 194-6.5°, coronary dilator and antispasmodic activity (CD) 0.9 (relative to papaverine-HCl as unity); 1-cyclopentylmethyl, 74%, m. 200-2°, CD 0.6; 1-β-cyclopentylethyl, 57%, m. 158-62.5°, CD 1; cyclohexyl, 41%, m. 166-8°, CD 1; 1-β-cyclohexylethyl, 56%, m. 203-4°, CD 0.3.

Journal of Organic Chemistry published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C9H8O4, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary