2-methoxy ethylamine

Caminati, W., K. Siam, J. D. Ewbank, and L. Schafer. 1987b. Interpretation of the Microwave Spectrum of 2-Methoxy Ethylamine Using Its Ab Initio Structures. J. Mol. Struct. 158, 237-247. 

Ethylenimine added dropwise during 2 hrs. with vigorous stirring and cooling at —5° to a soln. of BFg in abs. methanol, heated slowly in a water bath, refluxed 4 hrs., the volatiles removed by distillation, the residue treated gradually with KOH and heated j( -methoxy-ethylamine. Y 91%. F. e. and methods s. U. Harder, E. Pfeil, and K.-F. Zenner, B. 97, 510 (1964). 

Anhalonine and Lophophorine. Spath and Gangl showed that each of these alkaloids contains a methylenedioxy group and that the quarternary iodide prepared from dZ-anhalonine is identical with lophophorine methiodide so that lophophorine must be N-methylanhalonine. Anhalonine was synthesised from 3 4-methylenedioxy-5-methoxybenzaldehyde by condensation with nitromethane, reduction of the product to the corresponding -ethylamine, the acetyl derivative (VII) of which, on treatment with phosphoric anhydride, condensed to 6-methoxy-7 8-methylenedioxy-l-methyl-3 4-dihydrofsoquinoline, m.p. 60-2°. This, on reduction, furnished the corresponding tetrahydrofsoquinoline, which proved to be anhalonine (VIII), and on conversion to the quaternary methiodide the latter was found to be lophophorine (IX) methiodide. The possible alternative, 8-methoxy-6 7-methylenedioxy-l 2-dimethyl-l 2 3 4-tetrahydrofsoquinoline, was prepared by Freund s method and the methiodide shown not to be identical with lophophorine methiodide. 

A mixture consisting of 4 grams of 1,2,3,4-tetrahydro-4,4-dimethyl-7-methoxy-isochromane-dione-(1,3) (MP 95° to 97°C), 2.53 grams of 4-aminosulfonyl-phenyl-(2)-ethylamine and 150 ml of xylene was heated for 2 hours at its boiling point in an apparatus provided with a water separator. Thereafter, the reaction mixture was allowed to cool and was then vacuum-filtered, and the filter cake was recrystallized from n-propanoi in the presence of activated charcoal. 2.9 grams (58% of theory) of 1,2,3,4-tetrahydro-4,4-dimethyl-2-(p-amino-sulfonylphenyl-(2)-ethyl]-7-methoxy-isoquinolinedione-(1,3), MP 203° to 205°C, of the formula below were obtained. 

D) 4 -[N-Ethyi-1 "-Methyl-2 -(4" -Methoxyphenyl)Ethylamino]Butyi-3,4-Dimethoxybenzoate Hydrochloride 10.3 g of 4 -iodobutyl-3,4-dimethoxybenzoate and 11.0 g of N-ethyl-p-methoxyphenylisopropylamine (obtained by catalytic reduction of an alcoholic solution of an excess quantity (60%) of p-methoxy-phenyl-acetone, to which was added a 33% (weight-for-weight) aqueous solution of ethylamine, with Pt as a catalyst), were boiled in 200 ml of methyl ethyl ketone for 20 hours, cooled and the iodine ion was determined the reaction was found to be complete. Then the methyl ethyl ketone was evaporated in vacuo and the residue was dissolved in 300 ml of water and 30 ml of ether the layers were separated and the water layer was extracted twice more with 20 ml portions of ether. 

Ethanamme, 2-(diphenylmethoxy)-jV,vV-di-methyl- [Ethylamine, (2-diphenyl-methoxy)-A,Ar-dimethyl-, Diphenhydramine], 55, 3, 4... 

For the preparation of N- 2-(methoxyphenyl)cthyl ]-4-mcthylbcn-zenesulfonamide (1) from Ameba resins A and Ba-Bd, 100 mg (0.089 mmol) Ameba resin A was added to a glass peptide reaction vessel, suspended in 3.0 mL 1,2-dichloroethane (DCE note 2), and treated with 26 pL (0.18 mmol, 2.0 Eq.) 2-(4-methoxy-phenyl)ethylamine (note 2) and 38 mg (0.178 mmol, 2.0 Eq.) sodium triacetoxyborohydride (note 2). The suspension was shaken for 1 h treated with 5 mL MeOH filtered on a glass frit and washed with DCM (2x5 mL), DMF (2x5 mL), MeOH (2 x 5 mL), and DCM (2x5 mL). The resin was dried under vacuum (0.5 torr) at room temperature overnight. The resin was suspended in 1.5 mL DCM, treated with 155 pL (0.89 mmol, 10.0 Eq.) N,N-diisopropylethylamine (note 2) and 85 mg (0.445 mmol, 5.0 Eq.) p-toluenesulfonyl chloride (note 2), and shaken for 3.5 h. The reaction mixture was filtered on a glass frit, washed with DCM (2 x 5 mL), DMF (2x5 mL), MeOH (2x5 mL), and DCM (2 x 5 mL), and dried under vacuum (0.5 torr) at room temperature for 2h. The resin was treated with 2.5 mL of a solution of 5% trifluoroacetic acid (note 2) in DCM, shaken for 15 min, filtered on a glass frit, and washed with DCM (3x5 mL). The combined filtrate and washings were concentrated and dried under vacuum (0.5 torr) at room temperature overnight to afford 18.0 mg (66%) N- [2-(methoxyphenyl)ethyl] -4-methylbenzenesulfonamide (1). 

Trichocereus pachanoi Cactus Mescaline 3,4-dimethoxyphenyl- ethylamine 3-methoxy-tyramine... 

Benzylische Acyloxy-Gruppen wie z.B. in 4,7-Diacetoxy-6-methoxy-2-methyl-l,2,3,4-te-trahydro-isochinolin werden bei der Reaktion mit primaren Aminen unter milden Bedin-gungen durch eine Alkylamino- Oder Arylamino-Gruppe ersetzt gleichzeitig wird die zwei-te Acetoxy-Gruppe im Molekul hydrolysiert, so daB man mit Ethylamin bzw. Anilin 4-Ethylamino-7-hydroxy-6-methoxy-2-methyl- (82%) bzw. 4-Anilino-7-hydroxy-6-meth-oxy-2-methyl-l,2,3,4-tetrahydro-isochinolin (66%) erhalt1. 

N 19.72% crysts, mp 122°. Prepd from 2,4,6-trinitro-5-methoxy-m-xylene and ethylamine in ale... 

An attempt to utilize this conversion of amines into aldehydes in an isoquinoline synthesis was not successful.439 Instead, reaction between 2-(3,4-dimethoxyphenyl)ethylamine and isatin afforded only the spiro compound 150.439 Reaction between isatin and 2-(3-hydroxy-4-methoxyphenyl)ethylamine gave a mixture of two spiro compounds, while a reaction of isatin, this amine, and benzylamine gave 6-hydroxy-7-methoxy-l-phenyl-1,2,3,4-tetrahydroisoquinoline.439... 

B. Preparation of -methoxy-3-trimethylsiloxy-. 3-butadiene. Tri-ethylamine (575 g, 5.7 mol) is stirred mechanically in a three-necked flask (Note 1). To it is added 10.0 g (0.07 mol) of zinc chloride prepared as described above. The mixture is stirred at room temperature under nitrogen for 1 hr. A solution of 250 g (2.50 mol) of 4-methoxy-3-buten-... 

N 20.73% yel crysts, mp 98°. Prepd from ethylamine and 2,4,6 trinitro-3 methoxy-toluene in ale... 

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