Dimethylformamide dimethyl acetal → HCID 68466006, compound

HRID 506161Notes

Reaction equation

HRID 506161 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH:8]=[CH:9][CH:10]=1.[CH3:17][N:18]([CH:20](OC)OC)[CH3:19].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])CN>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12](=[O:16])[C:13]([C:14]#[N:15])=[CH:20][N:18]([CH2:17][C:32]3[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[C:34]([O:35][CH3:36])[CH:33]=3)[CH:19]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 79832VeratrylamineHCID 68466290HCID 68466290, compound

Product 1

HCID 68466006HCID 68466006, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-[3-(2-chloroethoxy)phenyl]-3-oxo-butyronitrile (16.0 g, 67.0 mmol) in 100 mL anhydrous DMF was added DMF-DMA (19.7 mL, 148 mmol) and TEA (9.4 mL, 67.0 mmol), and the solution was heated at 100° C. for 2.5 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2, passed through Magnesol® and concentrated. The crude material was then stirred with 3,4-dimethoxybenzylamine (11 mL, 74 mmol) in 100 mL of anhydrous toluene at reflux for 2 h. The reaction was cooled, concentrated in vacuo, and purified by flash chromatography on silica gel eluting with EtOAc to yield 11.8 g (41% yield) of 5-[3-(2-chloroethoxy)phenyl]-1-(3,4-dimethoxybenzyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. concentrationconcentrated
  4. temperatureat reflux for 2 h
  5. temperatureThe reaction was cooled
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-47ed42fe3e6f4aaa956a4826430414be
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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