Hydrochloric Acid → 1-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclohexylamine

HRID 1469277Notes

Reaction equation

HRID 1469277 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([NH:25]C(=O)OC(C)(C)C)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].Cl>C(O)C>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57515419HCID 57515419, compound

Product 1

HCID 575154201-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclohexylamineYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate (24.6 g, 56.1 mmol) in ethanol (100 mL) was added 2.7 M HCl in ethanol (150 mL). The solution was heated at 65° C. for 4 h, the was allowed to cool to rt overnight. A light brown precipitate was isolated by filtration and washed with ethanol. The precipitate was dissolved in water (100 mL) and NaOH was added until the pH=14. The mixture was extracted with dichloromethane (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to an oil that was dissolved in ethanol (100 mL). To the ethanol solution was added 2.7 M HCl in ethanol (18.7 mL). A pale tan solid crashed out of solution and was isolated by filtration and dried. The solid was dissolved in water (100 mL) and NaOH was added until the pH=14. The mixture was extracted with dichloromethane (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to yield 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanamine as a light yellow oil (15.1 g, 79%).

Workup

  1. temperatureto cool to rt overnight
  2. customA light brown precipitate was isolated by filtration
  3. washwashed with ethanol
  4. dissolutionThe precipitate was dissolved in water (100 mL)
  5. additionNaOH was added until the pH=14
  6. extractionThe mixture was extracted with dichloromethane (3×200 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil that
  10. dissolutionwas dissolved in ethanol (100 mL)
  11. additionTo the ethanol solution was added 2.7 M HCl in ethanol (18.7 mL)
  12. customwas isolated by filtration
  13. customdried
  14. dissolutionThe solid was dissolved in water (100 mL)
  15. additionNaOH was added until the pH=14
  16. extractionThe mixture was extracted with dichloromethane (3×200 mL)
  17. dry with materialdried over Na2SO4
  18. filtrationfiltered
  19. concentrationconcentrated

Sources & evidence

ORD record
ord-d8ad7c9574724a568e945d5a6ba1e324
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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