Hydrochloric Acid → HCID 57655914, compound

HRID 911661Notes

Reaction equation

HRID 911661 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][CH:12]=1)=O)(C)(C)C>O1CCOCC1.CO>[CH3:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH2:9])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656011HCID 57656011, compound

Product 1

HCID 57655914HCID 57655914, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (15 mL) to a stirred solution of N-(tert-butoxycarbonyl)-4-(3,3-dimethyl-butyl)-benzylamine (1.25 g, 4.29 mmol) in methanol (20 mL) and stir at room overnight. Concentrate in vacuo and wash the solid with diethyl ether. Suspend the solid in dichloromethane and saturated aqueous NaHCO3 and stir until both phases are clear (15 min). Extract the aqueous phase twice with dichloromethane. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to give the title compound as an oil (0.654 g, 80%) that was used without any further purification. MS (ES+) m/z: 192 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. washwash the solid with diethyl ether
  3. stirringsaturated aqueous NaHCO3 and stir until both phases
  4. custom(15 min)
  5. extractionExtract the aqueous phase twice with dichloromethane
  6. dry with materialDry the combined organic extracts over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e90bd23870a84565afd99a05d80f738a
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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