Hydrochloric Acid → HCID 59438391, compound

HRID 2177498Notes

Reaction equation

HRID 2177498 reaction equation
C(OC(=O)[NH:7][C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[N:10]([CH3:16])[CH2:9]1)(C)(C)C.Cl.CO>O1CCOCC1>[CH3:16][N:10]1[C:11]([CH3:15])([CH3:14])[CH2:12][CH2:13][C:8]([NH2:7])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59438451HCID 59438451, compound

Product 1

HCID 59438391HCID 59438391, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 50 mg (0.157 mmol) (1,6,6-Trimethyl-3-phenyl-piperidin-3-yl)-carbamic acid tert-butyl ester in 0.3 ml dioxane was added 0.39 ml (1.57 mmol) of a 4M HCl solution in dioxane at room temperature. After 30 minutes 0.3 ml methanol was added to dissolve the product. The mixture was stirred at room temperature for 5 hours. The solvent was removed in vacuo. The residue was dissolved in water. The aqueous layer was extracted twice with ethyl acetate and then basified with a 2M sodium carbonate solution. The aqueous layer was extracted 3 times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to provide 22 mg (64%) of the title compound as a brown oil. MS (m/e): 219.4 (M+H).

Workup

  1. dissolutionto dissolve the product
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. extractionThe aqueous layer was extracted 3 times with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ede25ba89ca64872b9da86687df7d552
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

Loading…