N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-

Base Information

• Chemical Name: N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-
• CAS No.: 85329-86-8
• Molecular Formula: C23H32N4O
• Molecular Weight: 380.533
• European Community (EC) Number: 687-649-9
• UNII: 114UFJ65CL
• DSSTox Substance ID: DTXSID40234529
• Nikkaji Number: J780.892E
• Wikidata: Q27251253
• Mol file: 85329-86-8.mol

Synonyms:Desethylcarbamoyl Cabergoline;85329-86-8;FCE-21590;N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-;Cabergoline specified impurity D;UNII-114UFJ65CL;114UFJ65CL;(6aR,9R,10aR)-N-[3-(dimethylamino)propyl]-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(6aR,9R,10aR)-N-(3-(Dimethylamino)propyl)-7-(prop-2-enyl)-4,6,6a,7,8,9,10,10a-octahydroindolo(4,3-fg)quinoline-9-carboxamide;Ergoline-8-carboxamide, N-(3-(dimethylamino)propyl)-6-(2-propenyl)-, (8beta)-;SCHEMBL1891628;DTXSID40234529;JJTHJEHDIBAMMM-YFVAEKQCSA-N;CABERGOLINE IMPURITY D [EP IMPURITY];Q27251253;N-[3-(dimethylamino)propyl]-6-allylergoline-8beta-carboxamide;(8beta)-N-(3-(dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide;ERGOLINE-8-CARBOXAMIDE, N-(3-(DIMETHYLAMINO)PROPYL)-6-(2-PROPENYL)-, (8.BETA.)-;N-(3-(DIMETHYLAMINO)PROPYL)-6-(2-PROPENYL)-ERGOLINE-8-CARBOXAMIDE, (8.BETA.)-

Chemical Property of N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-

Chemical Property:

• Vapor Pressure: 1.03E-14mmHg at 25°C
• Melting Point: 188-190°C
• Boiling Point: 607.7°C at 760 mmHg
• Flash Point: 321.3°C
• PSA: 54.86000
• Density: 1.13g/cm³
• LogP: 3.53020
• Storage Temp.: -20?C Freezer
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 380.25761166
• Heavy Atom Count: 28
• Complexity: 565

Purity/Quality:

99%min ^*data from raw suppliers

Desethylcarbamoyl cabergoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCNC(=O)C1CC2C(CC3=CNC4=CC=CC2=C34)N(C1)CC=C
• Isomeric SMILES: CN(C)CCCNC(=O)[C@@H]1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)CC=C
• Uses: A metabolite of Cabergoline, having affinity for D1 and D2 dopamine receptors in rat striatum

Technology Process of N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-

There total 6 articles about N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (72821-79-5) + 1-amino-3-(dimethylamino)propane (109-55-7) → (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide (85329-86-8)

Guidance literature:

In acetic acid; Heating;

DOI:10.1016/0223-5234(89)90087-1

Reference yield:

9,10-dihydrolysergic acid methyl ester (3006-19-7,5143-94-2,35470-53-2,77842-02-5,87247-99-2,96648-31-6,96648-32-7) → (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide (85329-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere

2: zinc / methanol; acetic acid / 1.08 h / 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C

4: acetic acid / 24 h / Reflux

With dmap; potassium carbonate; acetic acid; zinc; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1039/c3ra43417f

Reference yield:

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate (80993-64-2) → (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide (85329-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc / methanol; acetic acid / 1.08 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C

3: acetic acid / 24 h / Reflux

With potassium carbonate; acetic acid; zinc; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1039/c3ra43417f

upstream raw materials:

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

1-amino-3-(dimethylamino)propane

9,10-dihydrolysergic acid methyl ester

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate

Downstream raw materials:

cabergoline

(6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-N⁹-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate

Refernces

• 1、 Ashford, Scott W.,Henegar, Kevin E.,Anderson, Andrew M.,Wuts, Peter G. M.. "A practical synthesis of cabergoline". . p. 7147 - 7150. Retrieved 2007/10/03.