N-(4-Morpholinomethylphenylmethyl)acetamide hydrochloride → [4-(Morpholin-4-ylmethyl)phenyl]methanamine
Reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16]C(=O)C)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1>Cl>[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(4-Morpholinomethylphenylmethyl)acetamide hydrochloride (28.4 g) was dissolved in 4N hydrochloric acid (114 ml) and the mixture was refluxed under heating for 3 hr 15 min. The solvent was evaporated and ethyl acetate was added. The resulting crystals were collected by filtration. The obtained crystals were dissolved in water (40 ml) and potassium carbonate was added to saturation, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and, after drying, the solvent was evaporated under reduced pressure to give the objective 4-(morpholinomethyl)phenylmethylamine (17.4 g), melting point 47-49° C.
Workup
- temperaturethe mixture was refluxed
- temperatureunder heating for 3 hr 15 min
- customThe solvent was evaporated
- additionethyl acetate was added
- filtrationThe resulting crystals were collected by filtration
- dissolutionThe obtained crystals were dissolved in water (40 ml)
- additionpotassium carbonate was added to saturation
- extractionthe mixture was extracted with chloroform
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customafter drying
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-e6392a97e6fb4e04b10839553d0aeb70
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288061B1
Reaction notes
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