Acetonitrile → 2-(2-(Benzyloxy)phenyl)propan-2-amine

HRID 337071Notes

Reaction equation

HRID 337071 reaction equation
[CH3:1][C:2](C)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3](N)=O.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C(#[N:44])C>O>[CH3:1][C:2]([CH3:3])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:44]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 66689021alpha,alpha-Dimethyl-2-(phenylmethoxy)-benzeneacetamide

Product 1

HCID 666888502-(2-(Benzyloxy)phenyl)propan-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of α,α-dimethyl-2-(phenylmethoxy)-benzeneacetamide (Example 198c, 19.45 g) dissolved in acetonitrile (200 mL) and water (200 mL) was treated with (Bis(trifluoroacetoxy)iodo)benzene (31.1 g) under nitrogen. The resulting solution was stirred at 20° C. for 60 h. The reaction mixture was diluted with water (300 mL), and extracted with diethyl ether. The aqueous layer was basified at 0° C. with 2M NaOH solution and extracted with ethyl acetate. The organic was dried (MgSO4), filtered and evaporated to afford the subtitle compound (13.26 g).

Workup

  1. extractionextracted with diethyl ether
  2. customwas basified at 0° C. with 2M NaOH solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-71f9881114ac401d9b21162c65a30f03
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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