Triethylamine → 3-(cyclopentyloxy)-N-(2,6-difluorophenyl)-4-methoxybenzamide

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Reaction Steps

A stirred solution of 2,6-difluoroaniline (1.52 g) and triethylamine (1.19 g) in dichloromethane (50 mL) at room temperature is treated dropwise with a solution of 3-cyclopentyloxy-4-methoxybenzoyl chloride (3.0 g), that is prepared as described hereinafter in Reference Example 3) in dichloromethane (50 mL). The solution is stirred and heated at reflux for 4 hours, then it is cooled, washed with water and dried over magnesium sulfate. The solution is concentrated and the resulting residue is recrystallized from ethyl acetate, to give N-(2,6-difluorophenyl)-3-cyclopentyloxy-4-methoxybenzamide (1.9 g), m.p. 158-160° C. [NMR(CDCl3): 1.55-1.7(m,3H),1.8-2.05(m,5H),3.93(s,3H),4.85(m,1H), 6.9(d,1H),6.95-7.03(m,2H),7.2-7.3(m,1H),7.35(bs,1H), 7.45(q,1H),7.53(d,1H); Elemental analysis: C,65.1; H,5.6;F,10.4; N,4.2%; Calculated: C,65.7; H,5.5;F,10.9;N,4.0%].

Provenance & Evidence