493-92-5

Basic information

• Product Name: prolintane
• Synonyms: prolintane;1-(1-Propyl-2-phenylethyl)pyrrolidine;1-(α-Propylphenethyl)pyrrolidine;1-(alpha-Propylphenethyl)pyrrolidine;1211-28-5 (Hydrochloride);1-Phenyl-2-pyrrolidinylpentane;Brn 0144260;Einecs 207-784-5
• CAS NO: 493-92-5
• Molecular Formula: C₁₅H₂₃N
• Molecular Weight: 217.34982
• EINECS: 207-784-5
• Mol File: 493-92-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: bp0.5 105°; bp16 153°
• Flash Point: 123.3 °C
• Appearance: /
• Density: 0.963 g/cm³
• Vapor Pressure: 0.00116mmHg at 25°C
• Refractive Index: 1.529
• PKA: 10.62±0.20(Predicted)
• CAS DataBase Reference: prolintane(CAS DataBase Reference)
• NIST Chemistry Reference: prolintane(493-92-5)
• EPA Substance Registry System: prolintane(493-92-5)

Safety Data

• Hazardous Substances Data: 493-92-5(Hazardous Substances Data)

Usage

Description

Prolintane, also known as a CNS stimulant, is a compound that serves as an analeptic drug. It is characterized by its ability to act as a norepinephrine-dopamine reuptake inhibitor, which contributes to its stimulating effects on the central nervous system.

Uses

Used in Pharmaceutical Industry:
Prolintane is used as a CNS stimulant for its analeptic properties, which help in increasing alertness and counteracting the effects of certain central nervous system depressants. Its action as a norepinephrine-dopamine reuptake inhibitor makes it a potential candidate for the treatment of various conditions related to low arousal or diminished responsiveness, such as fatigue, drowsiness, or certain neurological disorders.

InChI:InChI=1/C15H23N/c1-2-8-15(16-11-6-7-12-16)13-14-9-4-3-5-10-14/h3-5,9-10,15H,2,6-8,11-13H2,1H3

Synthetic route

1-(1-benzylbut-3-enyl)pyrrolidine → Prolintane (493-92-5)

Conditions	Yield
With hydrogen In methanol under 3102.97 Torr;	92%

pyrrolidine hydrochloride (25150-61-2) + butyraldehyde (123-72-8) + alkali cyanide → Prolintane (493-92-5)

Conditions	Yield
With water Behandeln des erhaltenen 2-Pyrrolidino-valeronitrils mit Benzylmagnesiumchlorid in Tetrahydrofuran und Benzol;
With water Behandeln des erhaltenen 2-Pyrrolidino-valeronitrils mit Benzylmagnesiumchlorid in Tetrahydrofuran und Benzol;

1,2-epoxy-3-phenylpropane (4436-24-2) → Prolintane (493-92-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(l) iodide / tetrahydrofuran / 1.5 h / -78 - 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 4: hydrogen / methanol / 3102.97 Torr View Scheme

1-phenylpent-4-en-2-ol (61077-65-4) → Prolintane (493-92-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 3: hydrogen / methanol / 3102.97 Torr View Scheme

allylbenzene (300-57-2) → Prolintane (493-92-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12.5 h / 0 - 20 °C 2: copper(l) iodide / tetrahydrofuran / 1.5 h / -78 - 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 5: hydrogen / methanol / 3102.97 Torr View Scheme

Prolintane (493-92-5) → 1-(1-Benzyl-butyl)-pyrrolidin-2-on (35259-27-9)

Conditions	Yield
With potassium permanganate; 18-crown-6 ether In dichloromethane for 1h; Heating;	90%

Prolintane (493-92-5) → 1-(1-Benzyl-butyl)-pyrrol (139925-12-5)

Conditions	Yield
With o-tetrachloroquinone In toluene for 20h; Heating;	31%

methyl bromide (74-83-9) + Prolintane (493-92-5) → 1-methyl-1-(1-benzyl-butyl)-pyrrolidinium; bromide (132568-51-5)

Conditions	Yield
With acetone

Prolintane (493-92-5) → 1-(1-p-Hydroxy-benzyl-butyl)-pyrrolidin-2-on (40431-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / KMnO4, 18-crown-6 / CH2Cl2 / 1 h / Heating View Scheme

Prolintane (493-92-5) → N-(1-Benzyl-butyl)-4-amino-buttersaeure

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / KMnO4, 18-crown-6 / CH2Cl2 / 1 h / Heating 2: 96 percent / N KOH / methanol / 1 h / Heating View Scheme

Upstream product

• 25150-61-2 pyrrolidine hydrochloride 
• 123-72-8 butyraldehyde 
• 300-57-2 allylbenzene 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 4436-24-2 1,2-epoxy-3-phenylpropane 

Downstream Products

• 132568-51-5 1-methyl-1-(1-benzyl-butyl)-pyrrolidinium; bromide 
• 35259-27-9 1-(1-Benzyl-butyl)-pyrrolidin-2-on 
• 139925-12-5 1-(1-Benzyl-butyl)-pyrrol 
• 40431-15-0 1-(1-p-Hydroxy-benzyl-butyl)-pyrrolidin-2-on 

Relevant articles and documents

An alternative synthesis of the CNS stimulant Prolintane

An alternative synthesis of prolintane, a CNS stimulant, is reported using commercially available allylbenzene in good overall yield (32.3%). The key transformations include epoxidation, Grignard reaction, Mitsunobu and reduction protocols.