ChemicalBook CAS DataBase List 3-METHOXY-N,N-DIMETHYLBENZYLAMINE

3-METHOXY-N,N-DIMETHYLBENZYLAMINE synthesis

12synthesis methods

Product Name:3-METHOXY-N,N-DIMETHYLBENZYLAMINE
CAS Number:15184-99-3
Molecular formula:C10H15NO
Molecular Weight:165.23

591-31-1
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15184-99-3
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Yield:15184-99-3 444.9 grams (89.7%)

Reaction Conditions:

dimethyl amine in palladium on activated carbon;diethyl ether;ethanol;

Steps:

1 Preparation of 5-[[4-[(4-acetyl-3-hydroxy-2-propylphenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone

EXAMPLE 1 Preparation of 5-[[4-[(4-acetyl-3-hydroxy-2-propylphenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone 3-Methoxybenzaldehyde (408 g, 3.00 moles) was dissolved in ethanol and then hydrogenated by catalytic hydrogenation in the presence of 5% palladium on activated carbon (20 g) in the presence of dimethylamine (678 g of a 40% aqueous solution, 6.0 moles). The reaction was allowed to proceed overnight at room temperature. The solvents were then removed in vacuo and the residue was dissolved in diethyl ether. This solution was thrice washed with water and dried over sodium sulfate. The solvents were removed in vacuo. The residue was further purified by distillation (bp 90°-94° C.) to yield 444.9 grams (89.7%) of the intermediate 1-(N,N-dimethylamino)methyl-3-methoxybenzene. In two liters of tetrahydrofuran was dissolved 1-(N,N-dimethylamino)methyl-3-methoxybenzene (330 g, 2.0 moles) prepared supra.

References:

US5747517,1998,A

67-56-1 Synthesis