Dimethylamine → Zolmitriptan

HRID 128989Notes

Reaction equation

HRID 128989 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][C@H:14]3[CH2:18][O:17][C:16](=[O:19])[NH:15]3)[CH:11]=2)[NH:6][CH:5]=1)#N.[CH3:20][NH:21][CH3:22]>[Pd]>[CH3:20][N:21]([CH2:1][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][C@H:14]3[CH2:18][O:17][C:16](=[O:19])[NH:15]3)[CH:11]=2)[NH:6][CH:5]=1)[CH3:22]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 539136153-Des[2-(Dimethylamino)ethyl] Zolmitriptan Acetonitrile

Product 1

HCID 60857Zolmitriptan

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of the product from step (c) (1.3 g) and 10% w/w Pd/C (1.0 g) in 30% w/w ethanolic dimethylamine (25 ml) was hydrogenated for 24 hours and filtered through Hyflo. Fresh Pd/C (0.7 g) and ethanolic dimethylamine (5 ml) were added to the filtrate and hydrogenation continued for a further 16 hours. The mixture was filtered through a silica column using DCM/EtOH/NH4OH (40:8:1) as eluant to give the desired product as a colourless foam (0.3 g). Elemental analysis and 1H NMR were consistent with the proposed structure.

Workup

  1. filtrationfiltered through Hyflo
  2. additionFresh Pd/C (0.7 g) and ethanolic dimethylamine (5 ml) were added to the filtrate and hydrogenation
  3. waitcontinued for a further 16 hours
  4. filtrationThe mixture was filtered through a silica column

Sources & evidence

ORD record
ord-6f67568a44024be082bdee4cfe940466
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

Loading…