Cinacalcet IMpurity 7 synthesis

9synthesis methods

Product Name:Cinacalcet IMpurity 7
CAS Number:802918-47-4
Molecular formula:C22H24F3N
Molecular Weight:359.44

3-(3-TRIFLUOROMETHYL-PHENYL)-PROPYLAMINE

104774-87-0
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802918-49-6 Synthesis

802918-49-6
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802918-47-4
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Yield:802918-47-4 78%

Reaction Conditions:

Stage #1: 3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine;1-(5,6-dihydro-naphthalen-1-yl)-ethanonewith titanium(IV) isopropylate at 20;Neat (no solvent);
Stage #2: with sodium tetrahydroborate in methanol at 20; for 1 h;

Steps:

3; 6 Compound (2): [1-(5,6-Dihydro-naphthalen-1-yl)-ethyl])-[3-(3-trifluoromethyl-phenyl)-propyl]-amine

The mixture of 1-(5,6-dihydro-naphthalen-1-yl)-ethanone (9b) (172 mg, 1.0 mmol) and 3-(3-trifluoromethyl-pheny)-propylamine (13) (204 mg, 1.0 mmol) in titanium(IV) isopropoxide (1 mL) was stirred at room temperature overnight. Methanol (5 mL) was added followed by careful addition of sodium borohydride (55 mg, 2.0 mmol). The reaction mixture was stirred at room temperature for 1 hour, then evaporated to dryness. The crude product was purified by chromatography on silica gel, loaded with dichloromethane and 30% ethyl acetate in hexane. The pure fractions were combined and evaporated to give compound (2) as a colorless oil (279 mg, 78%).

References:

US7361789,2008,B1 Location in patent:Page/Page column 44; 52