Hydrochloric Acid → Zolmitriptan

HRID 1608997Notes

Reaction equation

HRID 1608997 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH:17]3OC(=O)N[CH2:18]3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:4].Cl.NC1C=CC(CC2[O:34][C:33](=[O:35])[NH:32]C2)=CC=1.CN1CCC(C2C3C(=CC=C(CC4COC(=O)N4)C=3)NC=2)CC1.Cl>>[CH3:4][N:3]([CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][C@H:17]3[CH2:18][O:35][C:33](=[O:34])[NH:32]3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 15233271(+/-)-3-(1-Methyl-4-piperidyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indoleHCID 701936045-[(4-Aminophenyl)methyl]-1,3-oxazolidin-2-one hydrochlorideHCID 70195317(+/-)-N,N-Dimethyl-2-[5-(2-oxo-1,3-oxazolidin-5-ylmethyl)-1H-indol-3-yl]ethylamine hydrochloride

Product 1

HCID 60857Zolmitriptan

Procedure

By steps identical to steps (d) to (f) of Synthetic Example 1 and Synthetic Example 2 or steps (d) and (e) of Synthetic Example 1 and Synthetic Example 3 and steps (e) to (h) of Synthetic Example 4, the product from step (a) was converted to (S)-N,N-diemthyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl]ethylamine.

Sources & evidence

ORD record
ord-fecd2ae2c9324ec79b8d7d4fdae52bd5
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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