Hydrochloride methanol → 3-(aminomethyl)-N,N-diethylaniline

HRID 2071004Notes

Reaction equation

HRID 2071004 reaction equation
CO.Cl.[CH2:4]([N:6]([CH2:22][CH3:23])[C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[CH2:10][NH:11]C(=O)OC(C)(C)C)[CH3:5]>>[NH2:11][CH2:10][C:9]1[CH:8]=[C:7]([CH:21]=[CH:20][CH:19]=1)[N:6]([CH2:4][CH3:5])[CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 68671365Tert-butyl 3-(diethylamino)benzylcarbamate

Product 1

HCID 392370373-(aminomethyl)-N,N-diethylanilineYield 77%

Procedure

MeOH.HCl (1.25 M, 11 ml, 13.9 mmol, 10 eq) was added to a flask charged with tert-butyl 3-(diethylamino)benzylcarbamate (0.3875 g, 1.4 mmol, 1 eq) at 0° C. under Ar. After stirring for 1.5 h at 0° C. the ice-bath was removed. After stirring at room temperature for 6 h, the solvent was removed in vacuo. The residue was stirred with saturated aqueous NaHCO3 for 30 min and extracted with CH2Cl2 (×2). The combined organics were dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo to yield 0.191 g (1.07 mmol, 77% yield) of the product.

Workup

  1. customwas removed
  2. customthe solvent was removed in vacuo
  3. stirringThe residue was stirred with saturated aqueous NaHCO3 for 30 min
  4. extractionextracted with CH2Cl2 (×2)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b2b0cd7513b74f04aa70b4ff2fcb77b7
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…