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

HRID 343916
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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
  • extractionThe remaining aqueous phase was extracted with ethyl acetate
  • customthe combined extracts evaporated in vacuo
  • Sources & evidence

    ORD record
    ord-63574b24f08040b983c7e8b1e3350c7d
    Source dataset
    uspto-grants-1999_01
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05863935

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes