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

HRID 485800Notes

Reaction equation

HRID 485800 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12](C=O)[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=[CH:2]1>O1CCOCC1>[N:1]1([CH2:6][CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 1

HCID 137267384[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde

Product 1

HCID 132811964-[3-(1H-imidazol-1-yl)propyl]piperidineYield 83.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde (2.12 g, 0.0095M) in dioxane (80 ml) and 2NHCl (11 ml) was refluxed for 51/2 hrs. After the reaction, the solvent was removed, water was added and the solution was basified with 2N NaOH to pH 10 and extracted with CH2Cl2 (3×50 ml). The extracts were concentrated to give an oil (1.55 g, 80%). The dihydrochloride salt of the 4[3-(1H-imidazol-1-yl)propyl]-piperidine which was crystallized from acetone has m.p. 184°-186° C.

Workup

  1. temperaturewas refluxed for 51/2 hrs
  2. customAfter the reaction
  3. customthe solvent was removed
  4. additionwater was added
  5. extractionextracted with CH2Cl2 (3×50 ml)
  6. concentrationThe extracts were concentrated

Sources & evidence

ORD record
ord-d3db796d2a99497482f2abf769b7bfb9
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

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