Benzene → HCID 13674885, compound

HRID 1650001Notes

Reaction equation

HRID 1650001 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:13][CH:14](Cl)[CH3:15])[C:10](=[O:12])[CH3:11].[CH3:17][NH:18][CH3:19].C1C=CC=CC=1>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:13][CH:14]([N:18]([CH3:19])[CH3:17])[CH3:15])[C:10](=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 241BenzeneHCID 674DimethylamineHCID 19855598HCID 19855598, compound

Product 1

HCID 13674885HCID 13674885, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.0 g (12.5 mmoles) of 1-[N-(2,6-dimethylphenyl)-acetamido]-2-chloro-propane and 9.4 ml of a 18 w/v % ethanolic dimethylamine solution is heated at 60° C. for 3 hours in a bomb. The mixture is cooled, admixed with 50 ml of benzene and 10 ml of water, and the organic phase is separated. The aqueous phase is extracted twice with 10 ml of benzene, each. The benzene solutions are combined, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 2.8 g (90.3%) of 1-[N-(2,6-dimethylphenyl)-acetamido]-2dimethylamino-propane are obtained as a thick, light yellow oil; b.p.: 140°-141° C./120 Pa. The hydrochloride monohydrate of the base melts at 170°-172° C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe organic phase is separated
  3. extractionThe aqueous phase is extracted twice with 10 ml of benzene
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-86180f1c106b44bc90639a1da0a38766
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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