Reaktion #170853

Reaktionsgleichung

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

2-phenylpyrrolidine

EDC

HOBT

DIPEA

→

title compound

(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(2-phenylpyrrolidine-1-carbonyl)piperidin-1-yl)methanone

Lösungsmittel

ethyl acetate

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschendiethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×)
2. 2
   TrocknenThe organic phase was dried with magnesium sulfate
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe resulting residue was dissolved in EtOAc
5. 5
   Sonstigeprecipitated out hexanes
6. 6
   Sonstigecollected over
7. 7
   Filtrationa filter
8. 8
   Waschenwashed with diethyl ether

Vorschrift

The following was added sequentially to DCM (2 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), DIPEA (0.07 mL, 0.378 mmol), EDC (30 mg, 0.151 mmol), HOBT (24 mg, 0.151 mmol), and 2-phenylpyrrolidine (0.023 mL, 0.151 mmol). The mixture was stirred for 18 h at rt, at which time the solution diluted with a 1:1 solution of ethyl acetate:diethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×). The organic phase was dried with magnesium sulfate and concentrated in vacuo. The resulting residue was dissolved in EtOAc and precipitated out hexanes, and then collected over a filter and washed with diethyl ether to give the title compound as a white solid. (Yield: 20 mg, 0.038 mmol, 30%) 1H NMR (400 MHz, CDCl3) 7.61, 7.43-7.05, 7.09-6.94, 6.58, 5.41, 5.06-4.82, 4.33, 3.83-3.60, 3.11-2.88, 2.50-2.22, 2.06-1.58, 1.16-0.82

Quelle