3-[1-(Dimethylamino)ethyl]phenol

Experimental procedure: To the solution of 50 percent sulfuric acid in water (400.0 [ML), ] was added at 10 to 15 C temperature, DL-methionine (124.9 gm, 0.837 moles) and stirred for 15 minutes. To this solution, was added [[1- (3-METHOXYPHENYL)] ethyl] dimethylamine (100.0 gm, 0.553 moles) at 10 to 15 C temperature within 2 hours and stirred for 30 minutes. Reaction mixture was then heated to 110 to 120C temperature for 28 hours. The reaction mixture was diluted with water, basified to pH 8.5 to 9.0 using ammonia solution and extracted with dichloromethane. Organic extract was then washed with water, charcoalized and concentrated. Hexane was then added to the residue and crude product filtered. b) Purification: Crude product was recrystallized from diisopropylether to give pure [1- (3- hydroxyphenyl) ethyl] dimethylamine (55.0 gm, 60 percent yield, Purity->99percent) melting range: 85 to [86C] temperature)Preparation of α-m-hydroxy phenylethyldimethylamine; N-methylation was carried out on α-m-hydroxy phenylethylamine (25g) with Paraformaldehyde (33g) in presence of Raney Nickel (3Og) in methanol (500ml) at 80N-Alkylation was carried on 3-hydroxy-l-phenylethylamine (lOgm) with 2 eq. of formaldehyde and 4 eq. of formic acid. The reaction was carried at 9OPreparation of α-m-hydroxy phenylethyldimethylamine; N-methylation was carried out on α-m-hydroxy phenylethylmethylamine (25g) with Paraformaldehyde (15g) in presence of Raney Nickel (3Og) in methanol(500ml) at 80°C and 10kg /cm12.00 g (0.06 mol) of compound Va, 10.00 g (0.06 mol) of potassium iodideAnd 10.60 g (0.09 mol) of potassium carbonate were added to a round bottom flask equipped with 200 ml of acetonitrile, The reaction was heated to 45 ° C, Throughout the reaction, 14.80 g (0.18 mol) of dimethylammonium hydrochloride were added in portions, TLC monitors the progress of the reaction.After the reaction was completed, the temperature was lowered to room temperature, Acetonitrile was concentrated to dryness, To the round-bottomed flask was added a suitable amount of water to dissolve the inorganic salt, After dilute hydrochloric acid to pH 5-6, and stirred for half an hour, The aqueous layer was extracted three times with ethyl acetate, the aqueous layer was adjusted to pH 8 with saturated sodium bicarbonate solution, And stirred for half an hour, after the aqueous layer was extracted with ethyl acetate three times, After the mixed ethyl acetate layer was dried over anhydrous sodium sulfate, Concentrated and evaporated to dryness to give a brown-yellow solid VIIa, yield 40.1percent.Into the reaction flask, the product 3-[1-(methylamino)ethyl]phenol III (11.8 g, 0.078 mol), formaldehyde (35-40percent, 10 ml) and formic acid (50 ml) were added and the reaction was heated to reflux. The reaction temperature is 120°C and the reaction is 12 hours.After completion of the reaction, the remaining formic acid was recovered under reduced pressure (as in Example 1).After recycling, add 30ml of water, and adjust the pH to 8-9 with 50percent sodium hydroxide solution, cool to 0°C, stirCrystallization, filtration, and drying over anhydrous magnesium sulfate gave 11.2 g of a product identified as 3-[1-(dimethylamino)ethyl]phenol II in a yield of 87percent.A mixture of 27.23 gram 3-hydroxyacetophenone (0.2 mol), 3.60 gram dimethylamine hydrochloride (0.4 mol), 10 gram activated molecular sieve (3A) and 10 gram dry MgSO4 is refluxed in dry methanol for 1-2 hours. Then, 18.85 gram NaCNBH3 is added to reaction mixture and the mixture is refluxed for additional 18-20 hours. After hot filtration of reaction mixture, methanol is distilled out under vacuum and the residue thus obtained is dissolved in water (250 mL). The content is acidified with conc. HCI to pH 1 and extracted with ethyl acetate (3x100 mL). The aqueous solution is basified to pH 8-9 using NaHCO3() and extracted with ethyl acetate (5x100 mL). Combined ethyl acetate extracts are washed with water dried over MgSO4 and concentrated under reduced pressure to give thick oil. This oil is dissolved in isopropyl ether (120 mL) under heating and allowed to cool to 0 °C. The crystalline solid obtained is filtered at the Buchner funnel under vacuum and dried in oven at 60°C to give the product as a light yellow crystalline solid. Yield obtained: 56.0percent. Purity by HPLC: 99percent. Mass spectrometry: peak at mlz 166 (M+1). 1H-NMR data in CD3OD: ö 1.34 (d, 3H), 2.17 (s, 6H), 3.22 (q, IH), 6.63-6.68 (m, IH), 6.69-6.79 (m, 2H), 7.10 (t, IH).A mixture of 27.23 g 3-hydroxyacetophenone (0.2 mol) (1), 3.60 g dimethylamine hydrochloride (0.4 mol), 10 g activatedmolecular sieve (3 Å) and 10 g dry MgSO4 was refluxed in drymethanol for 1–2 h. Then, 18.85 g NaCNBH3 was added to reactionmixture and the mixture was refluxed for additional 18–20 h. Afterhot filtration of reaction mixture, methanol was removed underreduced pressure and the residue thus obtained was dissolved inwater (250 mL). The content was acidified with concd HCl to pH1 and extracted with ethyl acetate (3 100 mL). The aqueous solutionwas basified to pH 8–9 using NaHCO3(s) (i.e., solid NaHCO3)and extracted with ethyl acetate (5 100 mL). Combined ethylacetate extracts were washed with water dried over MgSO4 andconcentrated under reduced pressure to give thick oil. This oilwas dissolved in isopropyl ether (120 mL) under heating andallowed to cool to 0 C. The crystalline solid obtained was filteredand dried to obtain a light yellow crystalline solid. Yield obtained:56.0percent. Purity by HPLC: 99percent. Mass spectrometry: peak at m/z 166(M+1)+. 1H NMR data in CD3OD: d 1.34 (d, 3H, ACHACH3), 2.17(s, 6H, CH3ANACH3), 3.22 (q, 1H, ANACHACH3), 6.63–6.68 (m, 1H, Ar-H), 6.69–6.79 (m, 2H, Ar-H), 7.10 (t, 1H, Ar-H).Example 4

Molecular Weight:165.23
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:165.115364102
Monoisotopic Mass:165.115364102
Topological Polar Surface Area:23.5
Heavy Atom Count:12
Complexity:136
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes