Acetophenone → HCID 2751242, compound
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6].C(C1C=CC=CC=1)(=O)C.C(OCC)=O.[Na].C(CC=O)(=O)C1C=CC=CC=1.Cl.CN>>[C:7]1([C:5](=[O:6])[CH:4]=[CH:3][NH:2][CH3:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
Procedure
In certain embodiments, a 3-methylamino-1-phenyl-1-propanol compound prepared by the method comprising: a) claisen condensation of acetophenone with ethyl formate leading to benzoylacetaldehyde sodium salt; b) condensation of the crude benzoylacetaldehyde sodium salt with an methylamine hydrochloride producing 1-phenyl-3-methylamino-2-propen-1-one; and c) converting 1-phenyl-3-methylamino-2-propen-1-one into 3-methylamino-1-phenyl-1-propanol by reacting 1-phenyl-3-methylamino-2-propen-1-one with sodium borohydride and acetic acid. Converting 1-phenyl-3-methylamino-2-propen-1-one into 3-methylamino-1-phenyl-1-propanol using sodium borohydride and acetic acid may comprise adding approximately 21 mmol of sodium borohydride to a solution comprising approximately 3.7 mmol of 3-methylamino-1-phenyl-2-propen-1-one in a glacial acetic acid solution producing a 3-methylamino-1-phenyl-1-propanol solution. The adding of sodium borohydride may be performed at about 1, 2, 3, 4, 5 to 10, 11, 12, 13, 14, 15° C. or more. The methods may further comprise adding approximately 240 mmol sodium hydroxide to the 3-methylamino-1-phenyl-1-propanol solution. The 3-methylamino-1-phenyl-1-propanol solution may be extracted with an ethyl acetate solution or another appropriate liquid or solution. The method may further comprise evaporating the solvent of the 3-methylamino-1-phenyl-1-propanol solution.
Sources & evidence
- ORD record
- ord-c94910e271e542c08c3273db4fd74373
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06846957B2
Reaction notes
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