Methyl iodide → 4-Iodo-α-(methoxymethyl)benzeneethanamine

HRID 76154Notes

Reaction equation

HRID 76154 reaction equation
[NH2:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH2:3][OH:4].I[CH3:14]>C1COCC1>[I:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH:2]([NH2:1])[CH2:3][O:4][CH3:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 217130182-Amino-3-(4-iodophenyl)propan-1-OL

Product 1

HCID 654783224-Iodo-α-(methoxymethyl)benzeneethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 12.0 g (43.3 mmol) 2-amino-3-(4-iodophenyl)-propan-1-ol (I41) and 350 mL THF is cooled down to 0° C. 3.81 g (95 mmol) NAH (60% in min. oil) are carefully added and the mixture is stirred at 0° C. for 30 min. 3.25 mL (52.0 mmol) iodomethane are added and cooling is removed. The reaction mixture is stirred at r.t. for 1 h. The mixture is poured onto water and extracted with EtOAc (2×). The combined organic layers are washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The compound is used without further purification.

Workup

  1. addition3.81 g (95 mmol) NAH (60% in min. oil) are carefully added
  2. temperaturecooling
  3. customis removed
  4. stirringThe reaction mixture is stirred at r.t. for 1 h
  5. additionThe mixture is poured onto water
  6. extractionextracted with EtOAc (2×)
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried with Na2SO4
  9. customthe solvent is removed in vacuo
  10. customThe compound is used without further purification

Sources & evidence

ORD record
ord-3eb18557454a4f82bcb5a98ee192ea61
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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