Triethylamine → N-(3-Isopropyl-2-propoxybenzyl)-N-methylacrylamide

HRID 1362290Notes

Reaction equation

HRID 1362290 reaction equation
[CH:1]([C:4]1[C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7]CN)([CH3:3])[CH3:2].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].[CH2:22]([N:24](CC)CC)C>C(Cl)Cl>[CH:1]([C:4]1[C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][N:24]([CH3:22])[C:17](=[O:20])[CH:18]=[CH2:19])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 66966658(3-Isopropyl-2-propoxybenzyl)methylamine

Product 1

HCID 59277555N-(3-Isopropyl-2-propoxybenzyl)-N-methylacrylamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-isopropyl-2-propoxybenzyl)methylamine (1.00 g, 4.51 mmol) in CH2Cl2 (40 mL) was added acryloyl chloride (0.43 mL, 4.96 mmol) drop-wise. After stirring for five minutes, triethylamine (0.69 mL, 4.96 mmol) was added and the solution was stirred for 5 hours. The solution was diluted with CH2Cl2 (50 mL), washed with H2O (3×50 mL) and brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (1.10 g, 88%) as a light yellow oil and a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 7.23-7.19 (m, 1H), 7.10-7.06 (m, 1H), 6.86-6.80 (m, 2H), 6.20-6.13 (m, 1H), 5.61-5.79 (m, 1H), 4.68-4.61 (m, 2H), 3.71-3.67 (m, 2H), 3.34-3.26 (m, 1H), 3.01-2.88 (m, 3H), 1.78-1.76 (m, 2H), 1.19-1.17 (m, 6H), 1.06-1.00 (m, 3H).

Workup

  1. stirringthe solution was stirred for 5 hours
  2. washwashed with H2O (3×50 mL) and brine (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c3c363cb7cb465f805239f407d721a5
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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