Benzylamine → N-benzyl-2,2-dimethoxypropionamide

HRID 1926231Notes

Reaction equation

HRID 1926231 reaction equation
[CH3:1][O:2][C:3]([O:9][CH3:10])([CH3:8])[C:4](OC)=[O:5].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC>[CH2:11]([NH:18][C:4](=[O:5])[C:3]([O:9][CH3:10])([O:2][CH3:1])[CH3:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 82339Methyl 2,2-dimethoxypropionate

Product 1

HCID 56980405N-benzyl-2,2-dimethoxypropionamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl 2,2-dimethoxypropionate (2.33 g, 15.7 mmol) and benzylamine (1.68 g, 15.7 mmol) in a 20 mL screw-capped vial was stirred at 55° C. for 12 d. To the reaction mixture, which mostly solidified upon cooling to ambient temperature was added hexane (5 mL), and the mixture was sonicated and stirred vigorously. The solid was filtered off, washed with hexanes, and dried in vacuo to give the title compound as off-white solid. 1H NMR (400 MHz, CDCl3): δ=7.38-7.25 (m, 5H), 7.08 (brs, 1H), 4.49 (d, J=5.6 Hz, 2H), 3.25 (s, 6H), 1.52 (s, 3H). MS(ES+): m/z=246.07 (58) [MNa+], 224.11 (58) [MH+], 192.12 (100) [MH+-MeOH], 160.11 (33) [MH+-2 MeOH]. HPLC: tR=2.78 min (polar—5 min, ZQ3).

Workup

  1. customscrew-capped vial
  2. temperatureupon cooling to ambient temperature
  3. customthe mixture was sonicated
  4. stirringstirred vigorously
  5. filtrationThe solid was filtered off
  6. washwashed with hexanes
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e86e1e1fa0e646049277435673707289
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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