4-Methylbenzylamine → 2,2-Dimethoxy-N-[(4-methylphenyl)methyl]acetamide

HRID 1926239Notes

Reaction equation

HRID 1926239 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1>CCOC(C)=O>[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4]([NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([CH3:10])=[CH:12][CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 660354-MethylbenzylamineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

Product 1

HCID 214193642,2-Dimethoxy-N-[(4-methylphenyl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl dimethoxyacetate (1.35 g, 9.96 mmol) and 4-methylbenzylamine (1.21 g, 9.98 mmol) in a sealable tube was heated in a microwave reactor to 140° C. for 50 min. The reaction mixture was diluted with EtOAc (≈60 mL), washed with diluted aq. HCl, water, sat. NaHCO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight to give the title compound as pale yellow oil. It was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=7.20-7.13 (AA′BB′, 4H), 6.82 (brs, 1H), 4.75 (s, 1H), 4.44 (d, J=5.6 Hz, 2H), 3.40 (s, 6H), 2.34 (s, 3H). MS(ES+): m/z=246.10 (43) [MNa+], 224.11 (91) [MH+], 192.14 (8) [MH+-MeOH], 160.06 (80) [MH+-2 MeOH]. HPLC: tR=2.84 min (polar—5 min, ZQ3).

Workup

  1. washwashed with diluted aq. HCl, water, sat. NaHCO3 solution, and brine
  2. dry with materialdried over MgSO4
  3. extractionThe EtOAc extract
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-30e69f5da49042dcb8fd09f1bd75271d
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…