80109-27-9

Basic information

• Product Name: Ciladopa
• Synonyms: Ciladopa;2-[4-[(S)-2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl]piperazin-1-yl]-2,4,6-cycloheptatrien-1-one
• CAS NO: 80109-27-9
• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.44
• Mol File: 80109-27-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 122-124 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Boiling Point: 571.6°C at 760 mmHg
• Flash Point: 299.5°C
• Appearance: /
• Density: 1.213g/cm³
• Vapor Pressure: 6.6E-14mmHg at 25°C
• Refractive Index: 1.593
• PKA: 13.97±0.20(Predicted)
• CAS DataBase Reference: Ciladopa(CAS DataBase Reference)
• NIST Chemistry Reference: Ciladopa(80109-27-9)
• EPA Substance Registry System: Ciladopa(80109-27-9)

Safety Data

• Hazardous Substances Data: 80109-27-9(Hazardous Substances Data)

Usage

Uses

Antiparkinsonian; dopaminergic agent.

Brand name

Tremerase (Wyeth-Ayerst).

InChI:InChI=1/C21H26N2O4/c1-26-20-9-8-16(14-21(20)27-2)19(25)15-22-10-12-23(13-11-22)17-6-4-3-5-7-18(17)24/h3-9,14,19,25H,10-13,15H2,1-2H3/t19-/m1/s1

Synthetic route

2-{4-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-ethyl]-piperazin-1-yl}-cyclohepta-2,4,6-trienone (80101-33-3) → AY 27110 (80109-27-9) + AY 27109 (80109-26-8)

Conditions	Yield
	A 0.95 g B 1.1 g

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone (1835-02-5) + theophylline sodium → AY 27110 (80109-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) K2CO3 / 1.) CH3CN, 80 deg C, 30 min, 2.) CH3CN, reflux, 25 h 2: sodium borohydride / methanol / 0.5 h 3: 0.95 g View Scheme

2-{4-[2-(3,4-Dimethoxy-phenyl)-2-oxo-ethyl]-piperazin-1-yl}-cyclohepta-2,4,6-trienone (80101-29-7) → AY 27110 (80109-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 0.5 h 2: 0.95 g View Scheme

2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one methanesulfonic acid salt (80100-70-5) → AY 27110 (80109-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) K2CO3 / 1.) CH3CN, 80 deg C, 30 min, 2.) CH3CN, reflux, 25 h 2: sodium borohydride / methanol / 0.5 h 3: 0.95 g View Scheme

AY 27110 (80109-27-9) + 4-chlorobenzoyl chloride (586-75-4) → (-)4-bromobenzoic acid, 1-(3,4-dimethoxyphenyl)-2-<4-(7-oxo-1,3,5-cycloheptatrien-1-yl)-1-piperazinyl>ethyl ester (83473-97-6)

Conditions	Yield
With triethylamine In dichloromethane for 3.5h; Ambient temperature;	69.8%

Upstream product

• 80101-33-3 2-{4-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-ethyl]-piperazin-1-yl}-cyclohepta-2,4,6-trienone 
• 80100-70-5 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one methanesulfonic acid salt 
• 80101-29-7 2-{4-[2-(3,4-Dimethoxy-phenyl)-2-oxo-ethyl]-piperazin-1-yl}-cyclohepta-2,4,6-trienone 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 

Downstream Products

• 83473-97-6 (-)4-bromobenzoic acid, 1-(3,4-dimethoxyphenyl)-2-<4-(7-oxo-1,3,5-cycloheptatrien-1-yl)-1-piperazinyl>ethyl ester 

Relevant articles and documents

Troponoids. 7. Chemistry and Dopamine Agonist Activity of Ciladopa and Related Aralkyltroponylpiperazines

A series of N-aralkyltroponylpiperazine derivatives were synthesized and evaluated for dopaminergic activity in rats rendered hypokinetic by the bilateral injection of 6-hydroxydopamine (6-OHDA) into the anterolateral hypothalamus.Several members of the series were active, and a structure-activity relationship is presented.A few selected compounds were also evaluated with regard to their ability to induce contralateral rotational behavior in rats with a unilateral 6-OHDA-induced lesion of the nigrostriatal dopamine (DA) pathway and to suppress elevated serum prolactin levels.The compounds were compared to bromocriptine.Some of the more potent analogues were also assayed for their binding affinity to dopamine (DA) and α1-adrenergic receptors.The results (a) established that the potency of some of the compounds were comparable or superior to that of bromocriptine, (b) indicated that potent dopaminergic activity was dependent on the presence of both a substituted phenyl and a troponylpiperazine moiety, and (c) confirmed that the dopaminergic activity depends on relative and absolute stereochemistry.