Hydrochloric Acid → 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 228038Notes

Reaction equation

HRID 228038 reaction equation
C(OC([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 231505174-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

Product 1

HCID 231507454-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-tert-Butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (80.0 mg) was mixed with a 4 mol/L dioxane solution of hydrogen chloride (1.2 mL) and the mixture was stirred at room temperature for 40 minutes. The crystallized product was collected by filtration and was suspended in water (0.8 mL). While the suspension was chilled in an ice bath, a 1 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added and the mixture was extracted with dichloromethane (4×3 mL). The dichloromethane extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This gave 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (39.8 mg) as a white solid.

Workup

  1. filtrationThe crystallized product was collected by filtration
  2. temperatureWhile the suspension was chilled in an ice bath
  3. additiona 1 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added
  4. extractionthe mixture was extracted with dichloromethane (4×3 mL)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d266e79336e437e84ad20eda97aaad6
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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