Water → Phenethylamine, N-butyl-alpha,alpha-dimethyl-

HRID 530422Notes

Reaction equation

HRID 530422 reaction equation
[CH3:1][CH2:2][CH2:3][NH:4][C:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:7])[CH3:6].[CH3:15]CN(CC)CC.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.O>ClCCl>[CH3:15][CH2:1][CH2:2][CH2:3][NH:4][C:5]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydride2×HCID 199973Cyclohexaneethylamine, alpha,alpha-dimethyl-N-propyl-

Product 1

HCID 200034Phenethylamine, N-butyl-alpha,alpha-dimethyl-Yield 134.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound D-3-7 (100 g, 380 mmol) and Et3N (76.8 g, 760 mmol) in dichloromethane (1.5 L), cooled to 0° C., is added triflic anhydride (Tf2O) (107.0 g, 380 mmol) via an addition funnel. Upon complete addition of Tf2O the solution is then warmed to room temperature for 5 h. The reaction mixture is then treated with H2O and dichloromethane and the organic phase is separated. The organic phase is washed with brine and dried over anhydrous Na2SO4. The mixture is then filtered and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography (using 20:1 petroleum ether:EtOAc) to provide compound D-3-8 (105 g, 70% yield).

Workup

  1. customthe organic phase is separated
  2. washThe organic phase is washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationThe mixture is then filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography (using 20:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-f1ee3640c5ea444c92e50318481aa987
Source dataset
uspto-grants-2016_05
Patent number
US09353090B2

Reaction notes

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