Ammonia → HCID 15586936, compound

HRID 225195Notes

Reaction equation

HRID 225195 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@:4]([CH3:20])(NN)[CH2:3]1.C[N:22]1[CH2:27][CH2:26]OCC1.C(Cl)(=O)C.[NH3:32].[OH2:33]>C(Cl)(Cl)Cl.C(#N)C>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:20][NH:32][NH:22][C:27](=[O:33])[CH3:26])[CH2:3]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 962WaterHCID 6367Acetyl chlorideHCID 79724-Methylmorpholine2×HCID 86737358HCID 86737358, compound

Product 1

HCID 15586936HCID 15586936, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

0.6 g (0.0021 moles) of 6-methyl-8β-hydrazino-methyl-ergoline are introduced, under vigorous stirring, into a solution of 0.28 ml (0.0025 moles) of N-methyl-morpholine in 60 ml of dry chloroform. When the solid dissolves completely, a solution of 0.184 g (0.0023 moles) of acetyl chloride in 2 ml of acetonitrile is added dropwise, within 5 minutes, to the mixture. After the addition the pH of the mixture is checked, and when it is lower than 6, N-methyl-morpholine is introduced. The reaction mixture is stirred at room temperature for one hour, thereafter it is diluted with 30 ml of water, and the pH of the mixture is adjusted to 8 with aqueous ammonia. The mixture is shaken, the phases are separated from each other, the organic phase is washed twice with water, dried, and evaporated to dryness in vacuo. The dry residue is crystallized from ethanol. The separated crystals are filtered off, washed with a small amount of cold (5° C.) ethanol, and dried in vacuo. 0.5 g (72.4%) of 6-methyl-8β-([N'-acetyl-hydrazino]-methyl)-ergoline are obtained; m.p.: 213°-215° C., [α]D20 =-38.7° (c=1, in 96% ethanol).

Workup

  1. dissolutionWhen the solid dissolves completely
  2. additionAfter the addition the pH of the mixture
  3. additionis introduced
  4. stirringThe mixture is shaken
  5. customthe phases are separated from each other, the organic phase
  6. washis washed twice with water
  7. customdried
  8. customevaporated to dryness in vacuo
  9. customThe dry residue is crystallized from ethanol
  10. filtrationThe separated crystals are filtered off
  11. washwashed with a small amount of cold (5° C.) ethanol
  12. customdried in vacuo

Sources & evidence

ORD record
ord-0f174f0e889646c2b5ac0499bcbcc0a3
Source dataset
uspto-grants-1980_11
Patent number
US04235912

Reaction notes

Loading…