Reaction #8470

Reaction equation

1-piperidinepropionic acid

WSC.HCl

1-hydroxybenzotriazole hydrate

product

2-(4′-aminophenyl)-8-methylimidazo[1,2-a]pyridine

N,N-diisopropylethylamine

→

title compound

Yield 23.9%

2-[4′-[3-(Piperidinyl)]propanamidophenyl]-8-methylimidazo[1,2-a]pyridine

Yield 23.9%

Solvents

dichloromethane

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONThe mixture was poured into a separatory funnel
2. 2
   Washwashed sequentially with an equal volume of 1 N sodium hydroxide and water
3. 3
   DryingThe organic phase was dried over sodium sulfate
4. 4
   Otherdecanted
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified via silica gel chromatography (methanol/dichloromethane)

Procedure

To a mixture of the product of Step B (330 mg) and N,N-diisopropylethylamine (0.28 mL) in dichloromethane (3 mL) and N,N-dimethylformamide (1 mL), was added 1-piperidinepropionic acid (256 mg), WSC.HCl (1-Ethyl-3-(3′dimethylaminopropyl)-carbodiimide.HCl) (312 mg), and 1-hydroxybenzotriazole hydrate (220 mg). The solution was stirred at ambient temperature for approximately 18 hours. The mixture was poured into a separatory funnel and washed sequentially with an equal volume of 1 N sodium hydroxide and water. The organic phase was dried over sodium sulfate, decanted and evaporated. The residue was purified via silica gel chromatography (methanol/dichloromethane) to yield the title compound (128 mg).

Source