![](/CAS/GIF/81409-90-7.gif)
Cabergoline synthesis
- Product Name:Cabergoline
- CAS Number:81409-90-7
- Molecular formula:C26H37N5O2
- Molecular Weight:451.6
![Des-N-allylcabergoline](/CAS/20211123/GIF/153415-36-2.gif)
153415-36-2
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![Allyl acetate](/CAS/GIF/591-87-7.gif)
591-87-7
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![Cabergoline](/CAS/GIF/81409-90-7.gif)
81409-90-7
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Yield:81409-90-7 92.3%
Reaction Conditions:
tetrakis(triphenylphosphine) palladium(0) in toluene at 20; for 2 h;
Steps:
5
EXAMPLE 5; Synthesis of 6-allyl-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-ergoline-8?- carboxamide (Cabergoline).; To a suspension of 9.0 g (21.87 mmol) N- [3- (dimethylamino) propyl] -N- [(ethylamino)carbonyl)-ergoline-8?-carboxamide (XIX) in 250 ml of toluene 0.5 g of tetrakis (triphenylphosphine) palladium (0) and 5 ml of allyl acetate was added, and the reaction mixture was stirred at ambient temperature for 2 hours. The resulting mixture was washed with 100 ml of water. The organic layer was dried over anhydrous sodium sulphate. The dried solution was concentrated in vacuum and the product was purified on a silica plug to give 9.1 g (92.3%) of the title compound. 1H NMR (DMSO-d6, TMS, 500MHz) 8 1.10 (t, 3H, J=7. 2Hz, CONHCH2CH3) ; 1.47 (q, 1H, J=12. 4Hz, Hp-9) ; 1.62-1. 72 (m, 2H, CONCH2CH2CH2N (CH3) 2) ; 2.15 (s, 6H, CONCH2CH2CH2N (CH3) 2); 2.20-2. 30 (m, 2H, CONHCH2CH2CH2N (CH3) 2); 2.32-2. 40 (m, 2H, H-5, Hp-7) ; 2.54 (dd, 1H, J=14. 3Hz, 11.2Hz, Hα-4) ; 2.68-2. 84 (m, 2H, Ha-9, H-10); 3.08 (ddd, 1H, J=11. 3Hz, 3. 1Hz, 1. 8Hz, Ha-7) ; 3.14-3. 22 (m, 2H, CONHCH2CH3) ; 3.26 (dd, 1H, J=14. 7Hz, 7.3Hz, HX-N (6) CH2CH=CH2) ; 3.28-3. 38 (m, 2H, Hp-4, H-8) ; 3.48 (dd, 1H, J=14. 7Hz, 5.8Hz, Hy-N (6) CH2CH=CH2) ; 3.58-3. 68 (m, 2H, CONCH2CH2CH2N (CH3) 2); 5.15 (d, 1H, J=10. 3Hz, HX-N (6) CH2CH=CH2) ; 5.24 (d, 1H, J=17. 2Hz, Hy-N (6) CH2CH=CH2) ; 5. 88-5. 98 (m, 1H, N (6) CH2CH=CH2) ; 6.75 (d, 1H, J=7. 0Hz, H-12); 6.97 (s, 1H, H-2); 7.01 (t, 1H, J=7. 5Hz, H-13); 7.13 (d, 1H, J=8. 0Hz, H-14) ; 9.04 (t, 1H, J=5. 0Hz, CONHCH2CH3) ; 10.60 (s, 1H, N (1) H).
References:
WO2005/85243,2005,A2 Location in patent:Page/Page column 22
![Desethylcarbamoyl Cabergoline](/CAS/GIF/85329-86-8.gif)
85329-86-8
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![Ethyl isocyanate](/CAS/GIF/109-90-0.gif)
109-90-0
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![Cabergoline](/CAS/GIF/81409-90-7.gif)
81409-90-7
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![Ergoline-8-carboxamide, N-[3-(dimethylamino)propyl]-1-[(1,1-dimethylethyl)dimethylsilyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-, (8β)- (9CI)](/CAS/20210305/GIF/909724-71-6.gif)
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![Cabergoline](/CAS/GIF/81409-90-7.gif)
81409-90-7
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![1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride](/CAS/GIF/25952-53-8.gif)
25952-53-8
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![6-Allyl-8beta-carboxyergoline](/CAS/GIF/81409-74-7.gif)
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![Cabergoline](/CAS/GIF/81409-90-7.gif)
81409-90-7
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![(82)-N-[[[3-(Dimethylamino)propyl]amino]carbonyl]-N-ethyl-6-(2-propen-1-yl)-ergoline-8-carboxamide](/CAS/20211123/GIF/81409-91-8.gif)
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![6-Allyl-8beta-carboxyergoline](/CAS/GIF/81409-74-7.gif)
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![Cabergoline](/CAS/GIF/81409-90-7.gif)
81409-90-7
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$39.00/1mg