Hydrochloric Acid → N-(5-(3-(N,N-Dimethylamino)propyloxy)-2-methylphenyl)tricyclo[3.3.1.13,7]decane-1-acetamide, hydrochloride

HRID 1066260Notes

Reaction equation

HRID 1066260 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].O[C:8]1[C:9]([CH3:28])=[C:10]([NH:14][C:15](=[O:27])[CH2:16][C:17]23[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]4)[CH2:18]2)[CH2:24]3)[CH:11]=[CH:12][CH:13]=1.[CH3:29][N:30]([CH2:32][CH2:33]C[Cl:35])[CH3:31].Cl>C(#N)C.CO.CCOCC>[ClH:35].[CH3:29][N:30]([CH2:32][CH2:33][CH2:1][O:4][C:12]1[CH:13]=[CH:8][C:9]([CH3:28])=[C:10]([NH:14][C:15](=[O:27])[CH2:16][C:17]23[CH2:18][CH:19]4[CH2:20][CH:21]([CH2:22][CH:23]([CH2:25]4)[CH2:24]2)[CH2:26]3)[CH:11]=1)[CH3:31]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 20660018N-(3-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Product 1

HCID 131722600N-(5-(3-(N,N-Dimethylamino)propyloxy)-2-methylphenyl)tricyclo[3.3.1.13,7]decane-1-acetamide, hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Caesium carbonate (1.31 g) was added to a suspension of N-(3-hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide (0.473 g, Example 26) in acetonitrile (35 ml) and the mixture heated at 80° C. for 5 minutes. After cooling to room temperature solid N,N-dimethyl-3-chloropropylamine (0.274 g) was added and the reaction heated at reflux overnight. The reaction was concentrated under reduced pressure and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethanol:triethylamine (95:4:1) to give a yellow gumn. This was dissolved in methanol (10 ml) and treated with an excess of ethereal hydrogen chloride is (1M, 5 equivalents). The solution was concentrated under reduced pressure to give a gum that was stirred for 2 days in ether (20 ml) to give a solid which was isolated by filtration (0.588 g).

Workup

  1. additionwas added
  2. temperaturethe reaction heated
  3. temperatureat reflux overnight
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customthe residue partitioned between dichloromethane (100 ml) and water (100 ml)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography over silica eluting with dichloromethane:ethanol:triethylamine (95:4:1)
  10. customto give a yellow gumn
  11. concentrationThe solution was concentrated under reduced pressure
  12. customto give a gum that
  13. customto give a solid which
  14. customwas isolated by filtration (0.588 g)

Sources & evidence

ORD record
ord-8f91771618514dcd9cbf4e3aaab3665f
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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