Nicotinic Acid → Testosterone nicotinate

HRID 1633223Notes

Reaction equation

HRID 1633223 reaction equation
S(Cl)(Cl)=O.[C:5]([OH:13])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[N:8][CH:7]=1.[CH3:14][C@@:15]12[C@@H:23](O)[CH2:22][CH2:21][C@H:20]1[C@@H:19]1[CH2:25][CH2:26][C:27]3[C@@:33]([CH3:34])([C@H:18]1[CH2:17][CH2:16]2)[CH2:32][CH2:31][C:29](=[O:30])[CH:28]=3>>[CH3:14][C@@:15]12[C@@H:23]([O:12][C:5]([C:6]3[CH:11]=[CH:10][CH:9]=[N:8][CH:7]=3)=[O:13])[CH2:22][CH2:21][C@H:20]1[C@@H:19]1[CH2:25][CH2:26][C:27]3[C@@:33]([CH3:34])([C@H:18]1[CH2:17][CH2:16]2)[CH2:32][CH2:31][C:29](=[O:30])[CH:28]=3

Participants

4

Reactant 3

HCID 938Nicotinic AcidHCID 6013TestosteroneHCID 24386Thionyl Chloride

Product 1

HCID 101826Testosterone nicotinate

Procedure

Thionyl chloride (2 ml) was added to 0.7 g (5.7 mmol) of nicotinic acid and the mixture was refluxed for 3 hrs. Excess thionyl chloride was distilled under vacuum. To the cold residue 10 ml of dry pyridine was added followed with 1.44 g (5.0 mmol) of testosterone. The mixture was heated while stirring over a boiling water bath for 3 hrs. Pyridine was distilled under vacuum and 5 ml of methanol was added to the oily residue. The mixture was cooled and the solid crystallized out was filtered and recrystallized from methanol/acetone mixture. Yield, 1.4 g (71%), m.p. 187°-188°.

Workup

  1. temperaturethe mixture was refluxed for 3 hrs
  2. distillationExcess thionyl chloride was distilled under vacuum
  3. additionTo the cold residue 10 ml of dry pyridine was added
  4. temperatureThe mixture was heated
  5. distillationPyridine was distilled under vacuum and 5 ml of methanol
  6. additionwas added to the oily residue
  7. temperatureThe mixture was cooled
  8. customthe solid crystallized out
  9. filtrationwas filtered
  10. customrecrystallized from methanol/acetone mixture
  11. customYield

Sources & evidence

ORD record
ord-923570ca4194454ea43c3323ebc6315f
Source dataset
uspto-grants-1984_10
Patent number
US04479932

Reaction notes

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