HCID 20239761, compound → HCID 13281205, compound

HRID 364746Notes

Reaction equation

HRID 364746 reaction equation
[N:1]1([CH2:6][CH2:7][CH:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH:10](C=O)[CH2:9]2)[CH:5]=[CH:4][N:3]=[CH:2]1>O1CCOCC1.Cl>[N:1]1([CH2:6][CH2:7][CH:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 20239761HCID 20239761, compound

Product 1

HCID 13281205HCID 13281205, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of hexahydro-4-[2-(1H-imidazol-1-yl)ethyl]-1H-azepine-carboxaldehyde (11 g, 0.05M) in dioxane (1.65 ml) and 2N HCl (82 ml) was heated and refluxed for 15 hrs. The solvent was removed, water (100 ml) was added and the resulting mixture was washed with methylene chloride (3×20 ml). After washing, the aqueous solution was basified with 4N NaOH to pH 12 and extracted with methylene chloride (4×75 ml). The combined extracts, dried over sodium sulfate, were stripped to yield hexahydro-4-[2-(1H-imidazol-1-yl)ethyl]-1H-azepine as an oil (6 g, 62% yield). This compound was characterized as dihydrochloride salt m.p. 176°-177° C.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 15 hrs
  3. customThe solvent was removed
  4. additionwater (100 ml) was added
  5. washthe resulting mixture was washed with methylene chloride (3×20 ml)
  6. washAfter washing
  7. extractionextracted with methylene chloride (4×75 ml)
  8. dry with materialThe combined extracts, dried over sodium sulfate

Sources & evidence

ORD record
ord-d365d3f6393946668de21d7aab231b00
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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