Nap-226-90 → Rivastigmine

Reaction equation

[CH3:1][N:2]([CH3:12])[C@H:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].C=O.[CH:15]([OH:17])=O>>[CH3:4][CH2:3][N:2]([C:15]([O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C@@H:3]([N:2]([CH3:1])[CH3:12])[CH3:4])[CH:6]=1)=[O:17])[CH3:1]

Participants

Reactant 2

HCID 445892Nap-226-90

HCID 18761834Formaldehyde formic acid

Product 1

HCID 77991Rivastigmine

Procedure

Patent publication WO2006/068386 describes a process for preparation of 3-(1-dimethylamino)phenol by subjecting (S)-3-(1-dimethylaminoethyl)phenol to N-methylation using formaldehyde/formic acid. The 3-(1-dimethylamino)phenol it is subjected to O-carbamoylation to form rivastigmine.

Sources & evidence

ORD record: ord-b2e956c09ec146da8ad2c63fadb17f25
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08852900B2

Reaction notes

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