Water → HCID 67945775, compound

HRID 1709654Notes

Reaction equation

HRID 1709654 reaction equation
[OH-].[K+].[CH3:3]I.[CH2:5]([N:8]1[C@H:22]2[C@@H:12]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]4[C:23]=3[C:20]([CH2:21]2)=[CH:19][NH:18]4)[CH2:11][C@H:10]([NH:24][C:25]2[CH:26]=[CH:27][C:28]3[O:32][CH2:31][CH2:30][C:29]=3[CH:33]=2)[CH2:9]1)[CH2:6][CH3:7].O>CS(C)=O>[CH3:3][N:18]1[C:17]2[C:23]3[C:20]([CH2:21][C@@H:22]4[C@@H:12]([C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]([NH:24][C:25]2[CH:26]=[CH:27][C:28]3[O:32][CH2:31][CH2:30][C:29]=3[CH:33]=2)[CH2:9][N:8]4[CH2:5][CH2:6][CH3:7])=[CH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 67946130HCID 67946130, compound

Product 1

HCID 67945775HCID 67945775, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

696 mg finely powdered KOH and 0.77 ml methyliodide are added to 4.1 g 6-n-propyl-8α-(2,3-dihydro-5-benzofuranylamino)-ergoline (example 9) in 25 ml dimethylsulfoxide. The reactive mixture is stirred for 5 hours, poured onto 150 ml H2O, extracted with ethyl acetate, dried over Na2SO4 and concentrated. The residue is chromatographed on 100 g silica gel using methylene chloride/methanol (98:2) as eluant. M.P.=137°-138° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is chromatographed on 100 g silica gel

Sources & evidence

ORD record
ord-a862150d39fe46adb4aece5ad11f1cf2
Source dataset
uspto-grants-1990_08
Patent number
US04950672

Reaction notes

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