Registry Number: 687603-66-3
Formula: C16 H21 N O3 CA Index Name: 1-Pentanone, 1-(1,3-benzodioxol-5-yl)-2-(1-pyrrolidinyl)- (9CI) Registry Number: 24622-62-6 Formula: C16 H21 N O3 . Cl H CA Index Name: 1-Pentanone, 1-(1,3-benzodioxol-5-yl)-2-(1-pyrrolidinyl)-, hydrochloride (9CI) Other Names: Valerophenone, 3',4'-(methylenedioxy)-2-(1-pyrrolidinyl)-, hydrochloride (8CI); 1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidino-1-pentanone hydrochloride Bibliographic Information 1-[(3,4-Methylenedioxy)phenyl]-2-pyrrolidino-1-alkanones as stimulants. (Boehringer Ingelheim G.m.b.H.). Brit. (1969), 7 pp. CODEN: BRXXAA GB 1149366 19690423 Patent written in English. Priority: DE 19650523. CAN 72:21608 AN 1970:21608 CAPLUS Patent Family Information Patent No. Kind Date Application No. Date GB 1149366 19690423 Priority Application DE 19650523 Abstract The title compds. (I) were prepd. by the reaction of a 3',4'-methylenedioxyphenyl a-haloalkyl ketone with either excess pyrrolidine in an inert solvent at <100ƒ, or NaOMe then pyrrolidine in an inert solvent. Thus, 22.1 g 1-(3,4-methylenedioxy-phenyl)-4-methylpentan-1-one in 100 ml C6H6 was brominated at room temp. with 5.1 ml Br in 15 ml C6H6, then evapd. in vacuo; a soln. of the residue in 100 ml C6H6 was treated with 40 ml Et2O, then with 12 g pyrrolidine, kept 5 hr at 50ƒ, worked up to give 71% I (R = H, R1 = Pr) HCl salt m. 236-8ƒ (alc.-Et2O). A soln. of 1.15 g Na in 30 ml MeOH was added to 13.2 g 1-(3,4-methylenedioxyphenyl)-2-bromo-2-methylpropan-1-one in 20 ml dry MeOH, the mixt. refluxed 1 hr worked up and treated with 6 g pyrrolidine, then refluxed 17 hr, and worked up to give I (R = R1 = Me) b0×015 150ƒ, HCl salt m. 188-90ƒ (alc.-Et2O). Similarly were prepd. the following I (R, R1, and m.p. of HCl salt gi ven): H, Et (III), 227-8ƒ (EtOH-Et2O); H, Bu (IV), 205.5-7. 0ƒ (iso-PrOH-Et2O); H, Pr (V), 229-31ƒ (iso-PrOH-Et2O); H, H, 234-5ƒ; H, Me, 242-3ƒ; H, C5H11 (VI), 201.5-3.5ƒ; H, C6H13, 184.5-6.0ƒ; H, iso-Pr, 266-7ƒ; H, sec-Bu, (HBr salt) 257-8ƒ; Me, Pr, (HBr salt) 151-2ƒ; Et, Et, (HBr salt) 166-7ƒ; and also 3',4'-methylenedioxy-2-morpholinoaceto-phenone, m. 219-20ƒ. I, esp. II, III, IV, V, and VI, are low toxicity central nervous system stimulants, and have hypertensive activity. The stimulation dose, LD50, and therapeutic index are for II, 0.20, 175 mg/kg, 875, IV, 0.54, 250 mg/kg, 463, and V, 0.96, 285 mg/kg, 296, resp., compared with benzedrine 1.95, 80 mg/kg, 42, and 1-(p-tolyl)-2-pyrrolidinopentanone, 1.6, 370 mg/kg, 231, resp. Patent Classifications IPC: C07D. Indexing -- Section 27 (Heterocyclic Compounds (One Hetero Atom) Nervous system (stimulants for central, (methylenedioxy)pyrrolidinylalkanophenones as) Bibliographic Information Pyrrolidino ketones. (Boehringer, C. H., Sohn). Fr. M. (1967), 5 pp. CODEN: FMXXAJ FR 5502 19671204 Patent written in French. Priority: DE 19650528. CAN 72:66801 AN 1970:66801 CAPLUS Patent Family Information Patent No. Kind Date Application No. Date FR 5502 19671204 Priority Application DE 19650528 Abstract Title compds. were prepd. as central nervous system stimulants. 1-(3,4-Methylenedioxyphenyl)-4-methyl-1-pentanone (22.1 g) in 100 ml C6H6 was brominated with 5.1 ml Br in 15 ml C6H6 at room temp., the mixt. evapd., the residue (31.3 g) dissolved in 100 ml C6H6, 40 ml Et2O and 12 g pyrrolidone (I) were added, and the mixt. heated 5 hr at 50ƒ to give 23 g 1-(3,4-methylenedioxyphenyl)-2-pyrrolidino-4-methyl-1-pentanone (II); HCl salt m. 236-8ƒ (EtOH-Et2O). A soln. of 13.2 g 1-(3,4-methylenedioxyphenyl)-2-bromo-2-methyl-1-propanone in 20 ml MeOH was refluxed 1 hr after addn. of 1.15 g Na in 30 ml MeOH. The mixt. was partitioned between H2O and Et2O, the Et2O evapd., and the residue refluxed 17 hr with 6 g I to yield 1-(3,4-methylenedioxyphenyl)-2-pyrrolidino-2-methyl-1-propanone; HCl salt m. 188-90ƒ (EtOH-Et2O). Several other compds. were prepd. and their phys. consts. given. Biol. test data were given. Patent Classifications IPC: A61K; C07D. Indexing -- Section 27 (Heterocyclic Compounds (One Hetero Atom) Ketones, preparation Role: PREP (Preparation) (phenyl pyrrolidinylalkyl) Bibliographic Information 1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidinoalkan-1-ones as central nervous system stimulants in warm blooded animals. Koeppe, Herbert; Ludwig, Gerhard; Zeile, Karl. (Boehringer Ingelheim G.m.b.H.). U.S. (1969), 5 pp. CODEN: USXXAM US 3478050 19691111 Patent written in English. Application: US 66-546197 19660429. CAN 77:114383 AN 1972:514383 CAPLUS Patent Family Information Patent No. Kind Date Application No. Date US 3478050 A 19691111 US 1966-546197 19660429 DE 1545591 A 19690807 DE 1965-B82155 19650528 Priority Application DE 1965-B82155 A 19650528 Abstract About 13 1-[3,4-(methylenedioxy)phenyl]-2-(1-pyrrolidinyl)alkanones (I, R = H, alkyl; R1 = alkyl) and their hydrochlorides or hydrobromides, useful as central nervous system stimulants, were prepd. from the bromo ketones (II). I (R = H; R1 = alkyl) were prepd. by heating II with pyrrolidine in C6H6-ether at 40-50ƒ or in C6H6 at reflux. I (R = alkyl; R1 = alkyl) were prepd. by refluxing II with MeONa in MeOH and refluxing the resulting epoxy compds. (III) with pyrrolidine. I.HCl and I.HBr were prepd. by acidifying I. Patent Classifications IPC: C07D; A61K. U.S.: 260326500. Indexing -- Section 28-5 (Heterocyclic Compounds (More Than One Hetero Atom) Supplementary Terms benzodioxolyl pyrrolidinyl alkanone; methylenedioxyphenyl pyrrolidinyl alkanone; pyrrolidinyl methylenedioxyphenyl alkanone; alkanone methylenedioxyphenyl pyrrolidinyl; ketone methylenedioxyphenyl pyrrolidinylalkyl; nervous system stimulant pyrrolidinylalkanone