Mezacopride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide-N-oxide, hydrochloride

HRID 3763

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:22])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][CH3:19])=[CH:13][C:12]=1[O:20][CH3:21])[CH2:2]2.C([O-])(=O)/C=C/C([O-])=[O:27]>>[ClH:17].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH+:9]([O-:27])[C:10](=[O:22])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][CH3:19])=[CH:13][C:12]=1[O:20][CH3:21])[CH2:2]2

Participants

Reactant 2

HCID 3047745Mezacopride

HCID 5460307Fumarate

Product 1

HCID 131715440N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide-N-oxide, hydrochloride

Procedure

N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxy-4-methylaminobenzamide, fumarate [1:1] is converted to the free base by partitioning with aqueous sodium hydroxide and methylene chloride. Using the procedure of Example 1, the free base is reacted with peracetic acid to obtain the N-oxide and finally with hydrogen chloride in isopropanol to give the hydrochloride.

Workup

customby partitioning with aqueous sodium hydroxide and methylene chloride
customthe free base is reacted with peracetic acid

Sources & evidence

ORD record: ord-bc32b8c0b4ec4edd970f899e38ffb207
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04722834

Linked notes

Loading…