Hydrochloric Acid → 1-[4-(Aminomethyl)-3-chlorophenyl]-3,3-dimethyl-1-butanone

HRID 911601Notes

Reaction equation

HRID 911601 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19][C:18]=1[Cl:30])=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[Cl:30][C:18]1[CH:19]=[C:20]([C:23](=[O:29])[CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH:21]=[CH:22][C:17]=1[CH2:16][NH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 57656316HCID 57656316, compound

Product 1

HCID 576559541-[4-(Aminomethyl)-3-chlorophenyl]-3,3-dimethyl-1-butanoneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (6 mL, 24 mmol) to a solution of N-(tert-butoxycarbonyl)-2-chloro-4-(3,3-dimethyl-butyryl)-benzylamine (700 mg, 2.06 mmol) in dichloromethane (25 mL) and stir overnight. Concentrate in vacuo and wash the solid obtained with diethyl ether. Suspend the solid into saturated aqueous NaHCO3 and stir for 30 min. Extract twice with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound as a yellow oil (477 mg, 97%).

Workup

  1. concentrationConcentrate in vacuo
  2. washwash the solid
  3. customobtained with diethyl ether
  4. stirringstir for 30 min
  5. extractionExtract twice with dichloromethane
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a380848ffd6a46198ee9aed3f266d6f7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…