Methane → N-(6-methylergolin-8beta-ylmethyl)succinimide
Reaction equation
[H-].[Na+].[C:3]1(=[O:9])[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.S(C1C=CC(C)=CC=1)(O[CH2:14][C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][CH:21]=3)[N:17]([CH3:31])[CH2:16]1)(=O)=O.C>C(O)C.CN(C)C=O>[CH3:31][N:17]1[C@H:18]2[C@@H:28]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:30]=3[C:20]([CH2:19]2)=[CH:21][NH:22]4)[CH2:29][C@@H:15]([CH2:14][N:7]2[C:6](=[O:8])[CH2:5][CH2:4][C:3]2=[O:9])[CH2:16]1Participants
7
Procedure
0.8 g of 50% sodium hydride in an oil was added in small portions to a mixture of 3.4 g of succinimide and 50 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 30 minutes. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were separated by filtration, and washed with water. The crystals thus obtained were treated with charcoal in ethanol and recrystallized from ethanol to obtain 0.9 g of the titled compound as colorless needles having a melting point of 233°-238° C. (with decomposition).
Workup
- temperaturewas then heated on a water bath for 30 minutes
- distillationThe solvent was distilled off under reduced pressure, and water
- additionwas added to the residue
- customThe precipitated crystals were separated by filtration
- washwashed with water
- customThe crystals thus obtained
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-ea454ccb77b3439989efa0917448d450
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04713457
Reaction notes
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