Reaction #312620

Reaction equation

(4-cyclopentyl-piperazin-1-yl)-(1H-indol-4-yl)-methanone

intermediate 2

(4-cyclopentyl-piperazin-1-yl)-(1H-indol-4-yl)-methanone

2-bromo-1-phenyl-propan-1-one

sodium-tert-butoxide

→

title compound

Yield 6.1%

2-[4-(4-Cyclopentyl-piperazine-1-carbonyl)-indol-1-yl]-1-phenyl-propan-1-one

Yield 6.1%

Solvents

THF

Conditions

Workup

1. 1
   OtherAfter evaporation to dryness the residue
2. 2
   workup.DISSOLUTIONwas dissolved in methanol/DMF
3. 3
   Othersubjected to purification by preparative HPLC on reversed phase
4. 4
   Washeluting with a gradient
5. 5
   Otherformed from acetonitrile/water/NEt3
6. 6
   OtherThe combined product fractions were evaporated

Procedure

A mixture of 29.8 mg (0.1 mmol) (4-cyclopentyl-piperazin-1-yl)-(1H-indol-4-yl)-methanone (intermediate 2), 32 mg (0.15 mmol) 2-bromo-1-phenyl-propan-1-one (commercially available) and 28.8 mg (0.3 mmol) sodium-tert-butoxide in 2 mL THF was shaken at room temperature for 16 h. After evaporation to dryness the residue was dissolved in methanol/DMF and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 2.6 mg of the title compound. MS (m/e): 430.5 (MH+).

Source