反应 #3141

反应方程式

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

溶剂

dichloromethane

dichloromethane

hydrochloric acid

dichloromethane

water

反应条件

后处理

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

实验过程

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.

来源