Zolmitriptan → 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan Acetonitrile

HRID 343916Notes

Reaction equation

HRID 343916 reaction equation
C[N:2]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C@H:16]3[CH2:20][O:19][C:18](=[O:21])[NH:17]3)[CH:13]=2)[NH:8][CH:7]=1)C>C(Cl)(Cl)Cl>[C:4]([CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C@H:16]3[CH2:20][O:19][C:18](=[O:21])[NH:17]3)[CH:13]=2)[NH:8][CH:7]=1)#[N:2]

Participants

3

Reactant 1

HCID 60857Zolmitriptan

Product 1

HCID 539136153-Des[2-(Dimethylamino)ethyl] Zolmitriptan AcetonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the product from step (b) (2.5 g) and polyphosphate ester (20.0 g) in chloroform (40 ml) was refluxed for 20 minutes. Ice was added to the cooled mixture and the chloroform evaporated in vacuo. The remaining aqueous phase was extracted with ethyl acetate and the combined extracts evaporated in vacuo to give the desired product as a pale yellow oil (1.8 g).

Workup

  1. additionIce was added to the cooled mixture
  2. customthe chloroform evaporated in vacuo
  3. extractionThe remaining aqueous phase was extracted with ethyl acetate
  4. customthe combined extracts evaporated in vacuo

Sources & evidence

ORD record
ord-63574b24f08040b983c7e8b1e3350c7d
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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