1-Phenethylamine → 2,2-Dimethoxy-N-(1-phenylethyl)acetamide

HRID 1926227Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of methyl dimethoxyacetate (2.10 g, 15.6 mmol) and α-methylbenzylamine (1.90 g, 15.7 mmol) was stirred at ambient temperature for 5 d and at 40° C. for 4 d. To the reaction mixture was added hexane (5 mL), and the mixture was sonicated. Two layers formed, but no solid precipitated, even upon cooling, and the hexane layer was withdrawn with a pipette. This was repeated twice. The residue was dissolved in EtOAc (≈100 mL), and the solution was washed with aqueous solutions of NH4Cl, NaHCO3, and brine, and dried over MgSO4. The solution was filtered and dried in vacuo overnight to give the title compound as pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ=7.38-7.30 (m, 4H), 7.29-7.24 (m, 1H), 6.80 (brs, 1H), 5.16 (dq, J=8.0, 6.8 Hz, 1H), 4.70 (s, 1H), 3.42 (s, 3H), 3.36 (s, 3H), 1.52 (d, J=6.8 Hz, 3H). MS(ES+): m/z=246.07 (64) [MNa+], 224.11 (78) [MH+], 192.11 (52) [MH+-MeOH], 160.10 (60) [MH+-2 MeOH]. HPLC: tR=2.76 min (polar—5 min, ZQ3).

Workup

customthe mixture was sonicated
customTwo layers formed
customno solid precipitated
temperatureeven upon cooling
customthe hexane layer was withdrawn with a pipette
dissolutionThe residue was dissolved in EtOAc (≈100 mL)
washthe solution was washed with aqueous solutions of NH4Cl, NaHCO3, and brine
dry with materialdried over MgSO4
filtrationThe solution was filtered
customdried in vacuo overnight

Sources & evidence

ORD record: ord-1ad1fa31ff544cb1ab13354d7531b38f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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