Ammonium Hydroxide → HCID 14653096, compound

HRID 1199668Notes

Reaction equation

HRID 1199668 reaction equation
[CH3:1][N:2]1[C:16]2[C:17]3[C:4]([CH2:5][C@@H:6]4[C@@H:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]([C:18]([OH:20])=O)[CH2:8][N:7]4[CH3:21])=[CH:3]1.P(Cl)(Cl)(Cl)=O.[NH2:27][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.[OH-].[NH4+]>CN(C)C=O>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH2:28][NH:27][C:18]([C@@H:9]2[CH2:10][C@H:11]3[C@@H:6]([CH2:5][C:4]4[C:17]5[C:16](=[CH:15][CH:14]=[CH:13][C:12]3=5)[N:2]([CH3:1])[CH:3]=4)[N:7]([CH3:21])[CH2:8]2)=[O:20])[CH:30]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 310183-PyridinemethanamineHCID 57156164HCID 57156164, compound

Product 1

HCID 14653096HCID 14653096, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One gram of 1,6-dimethylergoline-8-carboxylic acid was slurried with 40 ml of dimethylformamide under a nitrogen atmosphere. The mixture was cooled by means of an external ice/acetone bath. To the slurry were added 700 mcl of phosphorous oxychloride in dropwise fashion keeping the temperature below 0° C. After stirring for 30 minutes, 800 mcl of 3-(aminomethyl)pyridine were added. After stirring an additional two hours, the mixture was poured into approximately 200 ml of dilute ammonium hydroxide and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The residue was crystallized from ethyl acetate/hexane to provide 700 mg of the desired title product, m.p. 185°-187° C.

Workup

  1. temperatureThe mixture was cooled by means of an external ice/acetone bath
  2. customthe temperature below 0° C
  3. stirringAfter stirring an additional two hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6bf441c8ffa848fc9ccc0d3e82536de4
Source dataset
uspto-grants-1990_02
Patent number
US04902691

Reaction notes

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