2-Methylimidazole → 4-[3-(2-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

A mixture of 2-methylimidazole (2 g, 0.025M) and sodium hydride (1.2 g, 50% in mineral oil, 0.025M) in dimethylformamide (20 ml) was stirred at room temperature for 1/2 hr. The reaction mixture was then heated at 50° C. and the solution of 4(3-bromopropyl)piperidine carboxaldehyde (4.6 g, 0.02M) in dimethylformamide (20 ml) was added slowly. After completing the addition, the reaction was heated at 50° C. for 4 hrs and then solvent was removed in vacuo. Water (80 ml) was added to the residue and the mixture was extracted with methylene chloride. The combined extracts, dried over sodium sulfate, were stripped to dryness to yield an oil. The oil was purified on silica gel column, eluted with methanol chloroform (1:9 v/v) to give 4-[3-(2-methyl-1H-imidazol-1-yl)-propyl]-1-piperidinecarboxaldehyde (3.86 g, 88% yield).

1. temperatureThe reaction mixture was then heated at 50° C.
2. additionthe addition
3. temperaturethe reaction was heated at 50° C. for 4 hrs
4. customsolvent was removed in vacuo
5. additionWater (80 ml) was added to the residue
6. extractionthe mixture was extracted with methylene chloride
7. dry with materialThe combined extracts, dried over sodium sulfate
8. customto yield an oil
9. customThe oil was purified on silica gel column
10. washeluted with methanol chloroform (1:9 v/v)

ORD record

ord-69b08ba29c744cf2b276cc6ca9f95fcc

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04537969