S-(+)-N,N-Dimethyl-3-(1-naphthoxy)-3-(2-thienyl)-1-propylamine oxalate synthesis
- Product Name:S-(+)-N,N-Dimethyl-3-(1-naphthoxy)-3-(2-thienyl)-1-propylamine oxalate
- CAS Number:132335-47-8
- Molecular formula:C21H23NO5S
- Molecular Weight:401.48
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132335-47-8
General procedure for the synthesis of (S)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine oxalate from 1-fluoronaphthalene, oxalic acid and R-3-(dimethylamino)-1-(2-thiophenyl)-1-propanol: R-3-(dimethylamino)-1-(2-thiophenyl)-1-propanol (2.0 g, 0.011 mol) was was dissolved in dimethylacetamide (100 mL) and a suspension of 60% sodium hydride (463 mg, 0.012 mol) was added slowly and dropwise. The reaction mixture was heated at 70°C with stirring for 20 minutes. Subsequently, 1-fluoronaphthalene (1.27 mL, 0.012 mol) was added dropwise to the reaction system and heating was continued with stirring at 110 °C for 60 min. After completion of the reaction, the reaction mixture was diluted with water and extracted twice with ether. The organic phases were combined, washed sequentially with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the oily product (S)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine (3.28 g, 75.6% yield).
Yield:132335-47-8 84.2%
Reaction Conditions:
in Isopropyl acetate;water at 20; for 21 h;Product distribution / selectivity;
Steps:
10
Example 10; Preparation of (S)-N,N-dimethyl-(3-(1-naphthyloxy)-3-thien-2-yl)propylamine Oxalic Acid Salt(S)-N,N-dimethyl-(3-(1-naphthyloxy)-3-thien-2 yl)propylamine (10 g, 32.1 mmoles) was dissolved in isopropyl acetate (50 mL) at ambient temperature. A solution of oxalic acid dihydrate (3.64 g, 25.7 moles, 0.8 eq) in water (30 mL) was then added. The resulting mixture was stirred for 21 hours and filtered. The filter cake was washed with isopropyl acetate (10 mL) and dried under vacuum at 40° C. to yield 10.87 g of the product as a white solid (Yield: 84.2%; HPLC (peak area at 220 nm) oxalic acid 1.78%, 4-[3-dimethylamino-1-(2-thienyl)-1-propyl]naphthol 0.10%, 1-naphthol 0.35%, (S)-N,N-dimethyl-(3-(1-naphthyloxy)-3-thien-2-yl)propylamine 97.65%; Titration: 99.5%; Karl Fischer: 0.06%; XRD as shown in FIG. 1 (Form A); IR essentially as shown in FIG. 3 (Form A); TGA DSC as shown in FIG. 2, mp onset 152.6° C.).
References:
US2009/93645,2009,A1 Location in patent:Page/Page column 6
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