Water → N-((8a)-2,6-Dimethylergolin-8-yl)-2-ethyl-2-methylbutanamide

HRID 1461334Notes

Reaction equation

HRID 1461334 reaction equation
[CH3:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH2:18])[CH2:7][N:6]1[CH3:19].C(N(CC)CC)C.[CH3:27][C:28]([CH2:34][CH3:35])([CH2:32][CH3:33])[C:29](Cl)=[O:30].O>ClCCl>[CH3:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:29](=[O:30])[C:28]([CH2:34][CH3:35])([CH3:27])[CH2:32][CH3:33])[CH2:7][N:6]1[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11116219Butanoyl chloride, 2-ethyl-2-methyl-HCID 142776002,6-Dimethyl-8alpha-aminoergoline

Product 1

HCID 11089898N-((8a)-2,6-Dimethylergolin-8-yl)-2-ethyl-2-methylbutanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A supension of 68 g 2,6-dimethyl-8α-aminoergoline in 1.5 l dichloromethane are pre-cooled to 4° and treated with 78 ml triethylamine. The mixture is treated under stirring dropwise within 25 minutes with 40.5 g 2-methyl-2-ethyl-butyryl chloride. The mixture is stirred for 30 minutes, poured onto 3 l water, the organic phase is dried (Na2SO4) and concentrated. The residue is chromatographed on 800 g silica gel using dichloromethane/methanol (98:2) to yield the title compound, which is crystallised from diethyl ether, m.p. 191°-192°.

Workup

  1. additionThe mixture is treated
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on 800 g silica gel

Sources & evidence

ORD record
ord-62cfafeb32cb45de9506c968950b523f
Source dataset
uspto-grants-1991_12
Patent number
US05075318

Reaction notes

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