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With sodium hydroxide; hydrazine; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol In water for 5 h; Heating
General procedure: 3-dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride (50g, El equivalents) andtriethylene glycol (100 ml) were charged to the reactor at room temperature. 50percent NaOH (E2equivalents) was added while keeping the internal temperature at room temperature. 64percent hydrazine solution in water (E3 equivalents) was added dropwise followed by heating the reaction mixture to a temperature of 80±5°C for a period of 5 hours. Thereafter, water was distilled off in a vacuum of 30-40mbar at a temperature of 80±5°C. The precipitated salt was separated from the reaction mixture by filtration at a temperature of approximately 80°C andsubsequently washed with triethylene glycol brought to a temperature of approximately 80°C (20 Volpercent of the total amount of triethylene glycol).Bringing the reaction mixture to a temperature of 200±10°C for a period of about 5 hours gave crude 1-cyclopropyl-napthalene which was isolated by azeotropic distillation at a temperature of 190±10°C in a vacuum of 30-40mbar. For further purification and isolation ofthe obtained product water was added to the distillate and the product extracted with methyl tert.-butyl ether. The organic phase was washed with water and distilled in a vacuum of 50- lOOmbar at a temperature of 80°C.The isolated pure 1-cyclopropyl-naphtalene was obtained as clear, colorless or pale yellow liquid with a boiling point of 152°C at 13 Torr.
With sodium hydroxide In water; toluene at 20℃; for 0.416667 - 0.666667 h;
A. Preparation of a mixture of stereoisomeric forms of 6-bromo-α-r2- rdimethylamino>)ethyll-2-methoxy-α-l-naphthalenyl-β-phenyl-3-quinolineethanol.; (3-dimethylamino)-l'-propionaphthone-HCl (48.47 g; 183.8 mmol) was dissolved in water (157.5 g) and stirred for 5 to 10 minutes at room temperature. Sodium hydroxide (51.46 g; 386 mmol) was added as a 30 percent solution in water and the reaction mixture was stirred for 10 to 15 minutes. Toluene (105 g) was added and the mixture was stirred for 10 to 15 minutes followed by separation of the layers. To the organic layer, water (100 g) was added and stirring was continued for 10 to 15 minutes, followed by separation of the layers. The organic layer was concentrated in vacuo at 50 to 60 0C, yielding 98,2 percent of (3-dimethylammo)-l '-propionaphthone.
With hydrogenchloride; In ethanol; water; for 10h;Heating / reflux;
Preparation 62: 3-Dimethylamino-l-naphthalen-l-ylpropan-l-one hydrochlorideTo a solution of 1-acetonaphthone (1Og, 59mmol), paraformaldehyde (2.3g, 78mmol) and dimethylamine hydrochloride (6.36g, 78mmol) in ethanol (2OmL) was added concentrated HCl (0.5mL). The reaction was heated to reflux for 10hr, then cooled to rt and concentrated in vacuo. The residue was triturated with Et2O (2OmL) affording the title compound, m/z (ES+) = 228 [M+H]+; RT = 2.22min.
Preparation 63: 1-Naphthalen-l-ylpropenone3-Dimethylamino-l-naphthalen-l-ylpropan-l-one hydrochloride (Preparation 62, 15.47g, 59mmol) was dissolved in water (40OmL) and basified to pH9 with saturated Na2CO3 solution. The free base was extracted into EtOAc (3 x 15OmL), and the combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in MeOH (25mL) and cooled to 00C and iodomethane (8.4mL, 135mmol) was added. The reaction mixture was warmed to rt and stirred for lhr. The resulting solid was filtered and washed with Et2O (2 x 2OmL). The solid was stirred vigorously between Et2O (10OmL) and saturated NaHCO3 solution (10OmL) for 16hr. The layers were separated and the aqueous extracted into EtOAc (2 x 10OmL). The combined organic fractions were washed with IM HCl (10OmL), brine (15OmL), dried (MgSO4) and concentrated in vacuo affording the title compound, delta? (CDCl3): 6.06 (IH, d), 6.28 (IH, d), 6.97 (IH, dd), 7.55 (3H, m), 7.74 (IH, m), 7.91 (IH, m), 8.00 (IH, d), 8.35 (IH, m).
With sodium hydroxide; In water; toluene; at 20℃; for 0.416667 - 0.666667h;
A. Preparation of a mixture of stereoisomeric forms of 6-bromo-alpha-r2- rdimethylamino>)ethyll-2-methoxy-alpha-l-naphthalenyl-beta-phenyl-3-quinolineethanol.; (3-dimethylamino)-l'-propionaphthone-HCl (48.47 g; 183.8 mmol) was dissolved in water (157.5 g) and stirred for 5 to 10 minutes at room temperature. Sodium hydroxide (51.46 g; 386 mmol) was added as a 30 % solution in water and the reaction mixture was stirred for 10 to 15 minutes. Toluene (105 g) was added and the mixture was stirred for 10 to 15 minutes followed by separation of the layers. To the organic layer, water (100 g) was added and stirring was continued for 10 to 15 minutes, followed by separation of the layers. The organic layer was concentrated in vacuo at 50 to 60 0C, yielding 98,2 % of (3-dimethylammo)-l '-propionaphthone.
6.9 g
With sodium hydroxide; In water; toluene; at 20℃; for 0.166667h;
3-Dimethylamino-1-(naphthalen-1-yl)propan-1-onehydrochloride (11.2 g, 0.042 mol) was dissolved in distilled water(10 mL) in a 250 mL one-neck round-bottom fl ask equippedwith a magnetic stirrer. Toluene (100 mL) and a solution ofsodium hydroxide (1.8 g, 0.045 mol) in distilled water (10 mL)were added to the resulting solution. The emulsion thus formedwas vigorously stirred for 10 min at room temperature. The aqueous layer was separated, and the toluene layer was dried overmagnesium sulfate, fi ltered, and concentrated. A mobile oilyyellowish liquid was obtained in a yield of 9.6 g. The chromatographicretention time tchr = 10.34 min. The yield of 6 was 99%according to HPLC data and 1H NMR spectra. 1H NMR(CDCl3), delta: 2.95 (s, 6 H, 2-CH3); 3.47 (t, 2 H, CH2-CH2,J = 7.0 Hz); 3.75 (t, 2 H, CH2-CH2, J = 7.0 Hz); 7.60-8.50(m, 7 H, CHarom). MS, found: m/z 228.1 [M + H]+; C15H17NO;calculated M + H = 228.1.
With sodium hydroxide; hydrazine; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; In water; for 5h;Heating;
General procedure: <strong>[5409-58-5]3-dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride</strong> (50g, El equivalents) andtriethylene glycol (100 ml) were charged to the reactor at room temperature. 50% NaOH (E2equivalents) was added while keeping the internal temperature at room temperature. 64% hydrazine solution in water (E3 equivalents) was added dropwise followed by heating the reaction mixture to a temperature of 80±5C for a period of 5 hours. Thereafter, water was distilled off in a vacuum of 30-40mbar at a temperature of 80±5C. The precipitated salt was separated from the reaction mixture by filtration at a temperature of approximately 80C andsubsequently washed with triethylene glycol brought to a temperature of approximately 80C (20 Vol% of the total amount of triethylene glycol).Bringing the reaction mixture to a temperature of 200±10C for a period of about 5 hours gave crude 1-cyclopropyl-napthalene which was isolated by azeotropic distillation at a temperature of 190±10C in a vacuum of 30-40mbar. For further purification and isolation ofthe obtained product water was added to the distillate and the product extracted with methyl tert.-butyl ether. The organic phase was washed with water and distilled in a vacuum of 50- lOOmbar at a temperature of 80C.The isolated pure 1-cyclopropyl-naphtalene was obtained as clear, colorless or pale yellow liquid with a boiling point of 152C at 13 Torr.
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