Boehringer Ingelheim Patent for MDPV


Formula: C16 H21 N O3


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