Trifluoroacetic acid → 61381-04-2

HRID 220256Notes

Reaction equation

HRID 220256 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:20]([O:19][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][NH2:7])[CH:15]=[CH:14][C:13]=1[O:16][CH2:17][CH3:18])[CH3:21]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 60279062HCID 60279062, compound

Product 1

HCID 84069461381-04-2Yield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.5 g of [2-(3,4-diethoxy-phenyl)-ethyl]-carbamic acid tert.-butyl ester in 20 mL DCM were added 5 mL of TFA at 0° C. The reaction mixture was stirred at rt for 30 min when another 5 mL of TFA were added. After stirring for further 2 h, 1M NaOH solution was dropwise added. The mixture was extracted twice with DCM, washed with water and brine. The organic phase was dried over MgSO4 and concentrated in vacuo to yield 4.3 g of 2-(3,4-diethoxy-phenyl)-ethylamine as yellow oil.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted twice with DCM
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cdde387af6d4b729eb90f138101a6b2
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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