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

HRID 485819Notes

Reaction equation

HRID 485819 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13](C=O)[CH2:12][CH2:11]2)[CH:4]=[CH:5][N:6]=1>O1CCOCC1.Cl>[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 1

HCID 202397824-[3-(2-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

Product 1

HCID 202397544-[3-(2-methyl-1H-imidazol-1-yl)propyl]piperidineYield 68.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-[3-(2-methyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde (3.8 g, 0.016M) in dioxane (100 ml) and 2N HCl (25 ml) was heated and refluxed for 51/2 hrs. After this period, solvent was removed, and 1N NaOH (50 ml) was added to the residue. This mixture was then extracted with methylene chloride (5×50 ml). The combined extracts, dried over sodium sulfate, were stripped to dryness to yield 4-[3-(2-methyl-1H-imidazol-1-yl)propyl]piperidine (2.3 g, 65% yield).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 51/2 hrs
  3. waitAfter this period
  4. customsolvent was removed
  5. addition1N NaOH (50 ml) was added to the residue
  6. extractionThis mixture was then extracted with methylene chloride (5×50 ml)
  7. dry with materialThe combined extracts, dried over sodium sulfate

Sources & evidence

ORD record
ord-13b38aaaeeb54dc18c0c7d37c2a792c1
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

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