Methylamine → HCID 19874521, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH:5]([OH:34])[CH2:6][NH:7][CH:8]([CH3:33])[CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2O[CH:18]=[C:19]([O:23]CC3C=CC=CC=3)[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1.[CH3:38][NH2:39]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH:5]([OH:34])[CH2:6][NH:7][CH:8]([CH3:33])[CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[N:39]([CH3:38])[CH:18]=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1Participants
3
Procedure
A suspension of 2-[4-[2 [(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-benzyloxy-4H-pyran-4-one (1.0 g) in 33% ethanolic methylamine solution (15 ml), was heated to 120° in a sealed vessel for 18 hours. The solvent was evaporated in vacuo and the residue purified by column chromatography on silica using chloroform, then 10% methanol:chloroform as eluent. The resulting gum was dissolved in methanol and 2M hydrochloric acid was added dropwise to bring the pH to 1.5-2.0. The solution was then hydrogenated at room temperature and pressure over 10% palladium on charcoal. After filtration and evaporation of solvent in vacuo the residue was treated with 1.2M sodium hydrogen carbonate solution (5 ml), and extracted with ethyl acetate (3×50 ml), and dried (MgSO4). After filtration and evaporation of solvent the residue was triturated with acetone to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-1-methyl-1H-pyrid-4-one (0.7 g) as a (40:60) mixture of diastereoisomers.