Dimethylamine → HCID 14871689, compound

HRID 532099Notes

Reaction equation

HRID 532099 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)=O.[CH3:12][NH:13][CH3:14].[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH:2]([N:13]([CH3:14])[CH3:12])[CH3:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 114603-MethoxyacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 14871689HCID 14871689, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Patent publication WO2004/037771 describes reductive amination of 3-methoxy acetophenone in presence of dimethylamine, titanium isopropoxide and sodium borohydride to obtain [1-(3-methoxyphenyl)ethyl]dimethylamine, which is further demethylated using hydrobromic acid to obtain 3-(1-dimethylamino)phenol. This is further resolved using (S)-(+)camphor-10-sulfonic acid and reacted with carbamoyl chloride to obtain rivastigmine.

Sources & evidence

ORD record
ord-044ff2aebf0c4abebd6384fc038824ca
Source dataset
uspto-grants-2014_10
Patent number
US08852900B2

Reaction notes

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