454-14-8

Basic information

• Product Name: Cuscohygrine
• Synonyms: 1,3-bis[(2s)-1-methylpyrrolidin-2-yl]propan-2-one;cuscohygrine;1,3-bis(1-methyl-2-pyrrolidinyl)acetone;1,3-BIS(1-METHYL-2-PYRROLIDINYL)PROPANONE;Cuskhygrine;Hellaradine;1,3-Bis[1-methylpyrrolidin-2-yl]propan-2-one;C06521
• CAS NO: 454-14-8
• Molecular Formula: C₁₃H₂₄N₂O
• Molecular Weight: 224.34246
• Product Categories: Heterocycles
• Mol File: 454-14-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: bp23 169-170°; bp14 152°; bp2 118-125°
• Flash Point: 118 °C
• Appearance: /
• Density: d420 0.9733
• Vapor Pressure: 0.000531mmHg at 25°C
• Refractive Index: nD20 1.4832
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Soluble), Ethyl Acetate, Methanol (Slightly)
• Stability: Solutions are unstable.
• CAS DataBase Reference: Cuscohygrine(CAS DataBase Reference)
• NIST Chemistry Reference: Cuscohygrine(454-14-8)
• EPA Substance Registry System: Cuscohygrine(454-14-8)

Safety Data

• Hazardous Substances Data: 454-14-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear Colourless Oil

Uses

It was the main alkaloid found in medicinal plants Datura metel.

InChI:InChI=1/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

Synthetic route

1-methyl-pyrrolidin-2-one (872-50-4) + acetonedicarboxylic acid (542-05-2) → cuscohygrine (454-14-8)

Conditions	Yield
With lithium aluminium tetrahydride anschliessende Decarboxylierung;

acetonedicarboxylic acid (542-05-2) + 4-methylamino-butyraldehyde (7729-27-3) → cuscohygrine (454-14-8)

Conditions	Yield
With aqueous solution of pH 7 Erhitzen des Reaktionsprodukts unter vermindertem Druck;

1,3-bis-(1-methyl-pyrrol-2-yl)-acetone (857419-87-5) → cuscohygrine (454-14-8)

Conditions	Yield
With palladium; acetic acid Hydrogenation;
With acetic acid; platinum Hydrogenation;

chromium(lll) acetate (1066-30-4) + dihydrocuscohygrine (80408-55-5, 80408-56-6) → cuscohygrine (454-14-8)

Conditions	Yield
isomer(ic) II;
isomer(ic) I;

1-methyl-pyrrolidin-2-one (872-50-4) + acetonedicarboxylic acid (542-05-2) + diethyl ether (60-29-7) + lithium alanate → cuscohygrine (454-14-8) + (+-)-hygrine

Conditions	Yield
in gepufferter wss. Loesung;

cuscohygrine (454-14-8) + methyl iodide (74-88-4) → 1,1,1',1'-tetramethyl-2,2'-(2-oxo-propanediyl)-bis-pyrrolidinium; diiodide (59884-19-4, 62209-22-7)

Conditions	Yield
With ethanol im Druckgefaess;

cuscohygrine (454-14-8) → (+/-)-hygrine (45771-52-6)

Conditions	Yield
With hydrogenchloride at 180℃;
With potassium hydroxide; diethyl ether laengeres Stehen;
With potassium hydroxide 8-stdg. Kochen;

cuscohygrine (454-14-8) → (1-methyl-pyrrolidin-2-yl)-acetic acid ethyl ester (5370-14-9)

Conditions	Yield
With nitrogen oxides; sodium ethanolate at 10 - 15℃;

cuscohygrine (454-14-8) → n-Undecane (1120-21-4) + 6-undecanol (23708-56-7)

Conditions	Yield
With ethanol; sodium erschoepfende Methylierung des Reaktionsgemisches und folgende Hydrierung mit Wasserstoff und kolloidalem Platin in 50 prozentiger Essigsaeure;

cuscohygrine (454-14-8) → 1,3-bis-(1-methyl-pyrrolidin-2-yl)-acetone-hydrazone

Conditions	Yield
With ethanol; hydrazine hydrate

cuscohygrine (454-14-8) → N-methylproline (68078-09-1)

Conditions	Yield
With chromium(III) oxide; sulfuric acid

cuscohygrine (454-14-8) → dihydrocuscohygrine (80408-55-5, 80408-56-6) + α-dihydrocuscohygrine

Conditions	Yield
With sodium amalgam; water isomer(ic) II;
With ethanol; sodium at 80℃; Trennung ueber das Pikrat; isomer(ic) II;

cuscohygrine (454-14-8) → dihydrocuscohygrine (80408-55-5, 80408-56-6) + β-dihydrocuscohygrine

Conditions	Yield
With sodium amalgam; water isomer(ic) I;
With ethanol; sodium at 80℃; Trennung von der β-Form ueber das Pikrat; isomer(ic) I;

cuscohygrine (454-14-8) → (1-methyl-pyrrolidin-2-yl)-acetone-hydrazone + cuscohygrine-hydrazone

Conditions	Yield
With ethanol; hydrazine hydrate

cuscohygrine (454-14-8) → (RS)-1-methylpyrrolidine-2-acetic acid (5626-43-7, 52484-80-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrogen oxides; sodium ethylate / 10 - 15 °C 2: aq. barium hydroxide solution View Scheme

cuscohygrine (454-14-8) → 2-ethoxycarbonylmethyl-1,1-dimethyl-pyrrolidinium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrogen oxides; sodium ethylate / 10 - 15 °C 2: alcohol View Scheme

Upstream product

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 542-05-2 acetonedicarboxylic acid 
• 7729-27-3 4-methylamino-butyraldehyde 
• 60-29-7 diethyl ether 
• 857419-87-5 1,3-bis-(1-methyl-pyrrol-2-yl)-acetone 
• 1066-30-4 chromium(lll) acetate 
• 80408-55-5 dihydrocuscohygrine 

Downstream Products

• 80408-55-5 dihydrocuscohygrine 
• 1120-21-4 n-Undecane 
• 23708-56-7 6-undecanol 
• 59884-19-4 Cuscohygrin-dimethoiodid