2,6-Diethylaniline → N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline

HRID 1578917Notes

Reaction equation

HRID 1578917 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].Cl[CH2:13][CH:14]1[O:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:14]1[CH2:13][NH:5][C:4]1[C:6]([CH2:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 113692,6-DiethylanilineHCID 11430Potassium CarbonateHCID 109426251,3-Dioxepane, 2-(chloromethyl)-

Product 1

HCID 21548999N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Diethylaniline (75 grams), 2-chloromethyl1,3-dioxepane (15 grams), potassium carbonate (34 grams) and dimethylformamide (60 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of about 18 hours. After this time the mixture is filtered and distilled to yield the desired product N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 18 hours
  5. filtrationAfter this time the mixture is filtered
  6. distillationdistilled

Sources & evidence

ORD record
ord-fef4340d598c4b58946195c5c2b5f051
Source dataset
uspto-grants-1976_02
Patent number
US03940259

Reaction notes

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