Ammonia → 4-[4-((R)-3-Amino-2-hydroxy-propylamino)-phenyl]-morpholin-3-one hydrochloride
Reaction equation
[Cl:1][CH2:2][C@H:3]([OH:19])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][CH:7]=1.[NH3:20].C>>[ClH:1].[NH2:20][CH2:2][C@@H:3]([OH:19])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][CH:7]=1Participants
4
Procedure
30.00 g of 4-[4-((R)-3-chloro-2-hydroxy-propylamino)-phenyl]-morpholin-3-one (MW=284.75; 1 eq.) were added to 634 g of conc. aqueous ammonia (MW=17.03; 88 eq.). The reaction mixture was stirred for 4 h at room temperature. Then 3.0 g of charcoal were added and after 10 min of stirring, the suspension was filtered and the cake was washed with 90 mL of water. Filtrate and wash water were combined and concentrated in vacuo to a mass of 37 g. To the residue were added 107 mL of ethanol. The resulting suspension was stirred for 1 h at ambient temperature and then cooled to 0° C. After stirring for at least 2 h at this temperature, the product was isolated by filtration and the filter cake was washed with 75 mL of ethanol. After drying in vacuo at 30° C., 24.89 g of the crystalline title compound were isolated. Yield=78.3%.