Ammonia → HCID 13060631, compound

HRID 1415405Notes

Reaction equation

HRID 1415405 reaction equation
[Na].N.[NH2:3][CH2:4][C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:7]([CH3:21])[CH2:6]1.[CH3:22]I>CCOCC.C(O)C>[NH2:3][CH2:4][C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[N:12]([CH3:22])[CH:11]=3)[N:7]([CH3:21])[CH2:6]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 5360545SodiumHCID 10611049HCID 10611049, compound

Product 1

HCID 13060631HCID 13060631, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 8 ml. of dry ethanol and 10 ml. of dry ether is added dropwise, within 20 minutes to the stirred solution of 1.9 g. of metallic sodium in 300 ml. of liquid ammonia. Upon this procedure the initially deep blue solution turns gradually colorless. Thereafter 2.53 g. of dried 8β-aminomethyl-6-methyl-ergoline, prepared as described in Step B above, are added, the mixture is stirred until complete dissolution occurs (for 5 minutes), and then a solution of 6.6 g. of methyl iodide in 8 ml. of dry ether is added dropwise, within 5 minutes to the mixture at -40° C. The mixture is stirred at the same temperature for an additional 30 minutes, thereafter it is warmed cautiously and ammonia is removed in vacuo. The residue is dissolved in a mixture of 100 ml. of isopropanol and 400 ml. of chloroform, 150 ml. of water are added to the solution, and the pH of the aqueous phase is adjusted to 8 with acetic acid. The mixture is shaken, the organic phase is separated, and the aqueous phase is extracted with 3×100 ml. of a 1:4 mixture of isopropanol and chloroform. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue is subjected to chromatography using a column filled with 40 g. of silica gel in order to remove the impurities optionally present. A 30:2:11 mixture of chloroform, water and methanol is used as eluting agent.

Workup

  1. additionA mixture of 8 ml
  2. additionare added
  3. custom(for 5 minutes)
  4. stirringThe mixture is stirred at the same temperature for an additional 30 minutes
  5. temperatureit is warmed cautiously
  6. customammonia is removed in vacuo
  7. dissolutionThe residue is dissolved in a mixture of 100 ml
  8. additionof water are added to the solution
  9. stirringThe mixture is shaken
  10. customthe organic phase is separated
  11. extractionthe aqueous phase is extracted with 3×100 ml
  12. additionof a 1:4 mixture of isopropanol and chloroform
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. customevaporated
  16. additionfilled with 40 g
  17. customof silica gel in order to remove the impurities
  18. additionA 30:2:11 mixture of chloroform, water and methanol
  19. washas eluting agent

Sources & evidence

ORD record
ord-843f21c815ae4e7b8e5ac0de3b38c82e
Source dataset
uspto-grants-1977_01
Patent number
US04005089

Reaction notes

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