Reaction #1031

Reaction equation

DMF

cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

3-(4-fluorophenoxy)propyl bromide

triethylamine

→

title compound

Yield 91.8%

cis-N-[1-[3-(4-Fluorophenoxyl)propyl]-3-methoxy-4-piperidinyl]-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

Yield 91.8%

Solvents

Ethyl acetate

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   WashThe obtained mixture was washed with water thrice
3. 3
   Dryingdried over magnesium sulfate
4. 4
   OtherThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

Procedure

A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtained mixture was washed with water thrice, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane) to give 0.13 g of the title compound.

Source