反応 #3141

反応方程式

formic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butyl amine

N-methylmorpholine

→

title compound

4-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-formyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

溶媒

dichloromethane

dichloromethane

hydrochloric acid

dichloromethane

water

反応条件

後処理

1. 1
   その他The layers were separated
2. 2
   抽出the the aqueous phase was extracted with dichloromethane (10 mL)
3. 3
   洗浄The combined organic layers were washed (brine)
4. 4
   その他dried
5. 5
   その他evaporated
6. 6
   その他to afford material which
7. 7
   その他was purified by chromatography with dichloromethane:methanol (20:1) as eluent

実験手順

To a 0° C. solution of formic acid (0.09 mL) in dichloromethane (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g) and the mixture stirred for 15 minutes. To this mixture was added a solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butyl amine (0.40) and N-methylmorpholine (0.13 mL) in dichloromethane (5 mL). The mixture was allowed to warm to room temperature overnight, and was diluted with 1N hydrochloric acid (5 mL), dichloromethane, and water (5 mL). The layers were separated and the the aqueous phase was extracted with dichloromethane (10 mL). The combined organic layers were washed (brine), dried, and evaporated to afford material which was purified by chromatography with dichloromethane:methanol (20:1) as eluent, to give a hydrate of the title compound (0.206 g); mp 108°-110° C.; NMR: 8.1-7.5 (m,6), 7.3 (m,6), 4.75-4.40 (m,2), 3.75-3.3 (m,4), 3.3-3.0 (m,4), 2.85 (m,1), 1.95 (s,3), 2.25-1.80 (m,4); MS: m/z=688(M+1,100%); TLC: Rf =0.46 (10:1 dichloromethane:methanol). Analysis for C33H33Cl2F6N3O2.1.50 H2O: Calculated: C, 55.39; H, 5.07; N, 5.87; Found: C, 55.38; H, 4.77; N, 5.84.

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