反応 #62023

反応方程式

1-isopropyl-piperazine dihydrochloride

5-(4-Isopropyl-piperazine-1-carbonyl)-1-methyl-1H-pyrrole-3-carbaldehyde

4-Formyl-1-methyl-1H-pyrrole-2-carboxylic acid

lithium

→

title compound

(4-Isopropyl-piperazin-1-yl)-(1-methyl-4-piperidin-1-ylmethyl-1H-pyrrol-2-yl)-methanone

溶媒

DCM

thionyl chloride

DCM

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux under nitrogen for 1.5 h
3. 3
   濃縮The reaction mixture was carefully concentrated
4. 4
   その他to remove residual HCl
5. 5
   濃縮The mixture was concentrated
6. 6
   その他to yield the crude product (3.78 g), which
7. 7
   その他was purified on silica gel column

実験手順

5-(4-Isopropyl-piperazine-1-carbonyl)-1-methyl-1H-pyrrole-3-carbaldehyde. 4-Formyl-1-methyl-1H-pyrrole-2-carboxylic acid, lithium salt, (1.08 g.) was diluted with thionyl chloride (20 mL) and heated at reflux under nitrogen for 1.5 h. The reaction mixture was carefully concentrated. The residue was co-evaporated with toluene (3×) to remove residual HCl, and then was kept under vacuum for 2 h. Separately, a solution of 1-isopropyl-piperazine dihydrochloride (1.21 g, 6.00 mmol) in DCM (50 mL) was cooled to 0-5° C. TEA (2.23 mL, 24.0 mmol) was added slowly, followed by the above acid chloride solution in DCM (50 mL). The resulting mixture was allowed to stir overnight at rt. The mixture was concentrated to yield the crude product (3.78 g), which was purified on silica gel column using 2-6% 2 M NH3 in MeOH/DCM to yield the title compound (0.20 g).

出典