반응 #50582

반응 방정식

water

N-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-yl]-N-methylheptanamide hydrochloride

potassium carbonate

piperidine

→

title compound

수율 22.4%

N-[4,4-bis(trifluoromethyl)-4,5-dihydro-1-methyl-2-[4-(1-piperidinyl)phenyl]-1H-imidazol-5-yl]-N-methylheptanamide, hydrochloride

수율 22.4%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도The reaction mixture was heated at 145° overnight under nitrogen
2. 2
   추출extracted with ether
3. 3
   세척The ether layer was washed with 1N HCL
4. 4
   기타to give unreacted
5. 5
   추출it was extracted with ether
6. 6
   세척The organic layer was washed with water and saturated sodium chloride
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축concentrated under vacuum
9. 9
   workup.ADDITIONThe residue was treated with HCl in ether

실험 절차

To a solution of N-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-yl]-N-methylheptanamide hydrochloride (0.20 g, 0.4 mmole) in dimethyl sulfoxide (5 mL) was added potassium carbonate (0.29 g, 1.2 mmole) and piperidine (0.10 g, 1.2 mmole). The reaction mixture was heated at 145° overnight under nitrogen. The solution was cooled to room temperature, poured into water and extracted with ether. The ether layer was washed with 1N HCL to give unreacted starting material. The aqueous layer was made basic and it was extracted with ether. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under vacuum. The residue was treated with HCl in ether to give the title compound (50 mg, 22%) as a semi solid: MS m/e 521 (M+ +H); 1H NMR (CDCl3 /TMS) δ 0.90(m,3H,CH3), 1.30(m,8H,(CH2)4), 1.67(m,6H,(CH2)3), 2.40(t,2H,CH2), 2.90(s,3H,NCH3), 2.97(s,3H,NCH3), 3.30(m,4H,2CH2), 6.53(s,1H,CH), 6.90(d,2H,Harom), 7.53(d,2H,Harom).

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