Hydrochloric Acid → N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide

HRID 1014391Notes

Reaction equation

HRID 1014391 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][C:4]([N:6]([CH3:23])[C:7]1[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:12]=1)=[O:5].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[NH2:13][C:11]1[CH:12]=[C:7]([N:6]([CH3:23])[C:4](=[O:5])[CH2:3][N:2]([CH3:24])[CH3:1])[CH:8]=[CH:9][C:10]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 594420081,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate

Product 1

HCID 59441934N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamideYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate (2.01 g, 5.96 mmol) in 1,4-dioxane (40 ml) was treated with 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) and stirred for 3 hours. Additional 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) was added and the reaction was stirred for 16 hours. The solution was poured into ethyl acetate, diluted with water, and neutralized by careful addition of solid potassium carbonate. The aqueous layer was washed with chloroform and the organic layers were combined, dried over sodium sulfate, filtered, and taken to a residue under reduced pressure to afford N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide (1.19 g, 5.01 mmol, 84% yield) as a tan oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.78 (d, J=8.2 Hz, 1 H), 6.48 (d, J=2.4 Hz, 1 H), 6.41 (d, J=8.2 Hz, 1 H), 4.91 (br. s., 2 H), 3.77 (s, 3 H), 3.05 (s, 3 H), 2.82 (s, 2 H), 2.12 (s, 6 H).

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. washThe aqueous layer was washed with chloroform
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c5610577d9014f6f94c291d1a2475b68
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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