Ammonia → 1-(1-Imidazolyl)-4-cyclohexylisoquinoline

HRID 1657586Notes

Reaction equation

HRID 1657586 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[NH2-].[Na+].N.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12][N:11]=1>O1CCOCC1>[N:1]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 795ImidazoleHCID 24533Sodium amideHCID 215349111-Chloro-4-cyclohexyl-isoquinoline

Product 1

HCID 215349171-(1-Imidazolyl)-4-cyclohexylisoquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.4 g (50 mmoles) of imidazole were allowed to react with 1.9 g (49 mmoles) of sodium amide in 50 ml of absolute dioxane until the evolution of ammonia was finished. Then 9 g (37 mmoles) of 1-chloro-4-cyclohexyl-isoquinoline were added and the solvent was evaporated. The reaction mixture was heated for 3 hours to 140° C, distributed between methylene chloride and water and the organic phase was evaporated after having been dried over magnesium sulfate. The oily crude product was taken up in 30 ml of ether and crystallized upon trituration. M.p. 92° to 93° C, hydrochloride M.p. 228° to 229° C.

Workup

  1. customthe solvent was evaporated
  2. temperatureThe reaction mixture was heated for 3 hours to 140° C
  3. customthe organic phase was evaporated
  4. dry with materialafter having been dried over magnesium sulfate
  5. customcrystallized upon trituration

Sources & evidence

ORD record
ord-ce4a84a585cd44da96842d995632aada
Source dataset
uspto-grants-1976_06
Patent number
US03961062

Reaction notes

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