Dimethylamine, hydrochloride → HCID 59847703, compound

HRID 1041856Notes

Reaction equation

HRID 1041856 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([F:11])[CH:5]=1.Cl.[CH3:14][NH:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:15]([CH3:16])[CH3:14])=[C:6]([F:11])[CH:5]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 2775358Methyl 3,4-difluorobenzoate

Product 1

HCID 59847703HCID 59847703, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 38.7 g (225 mmol) 3.4-difluoro-benzoic acid methyl ester (Apollo) and 600 ml dimethylsulphoxid were added 22.3 g (270 mmol) dimethylamine hydrochloride and 65.4 g (473 mmol) potassium carbonate. The reaction mixture was stirred for 5 h at 55° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude product 3a was obtained in 71% yield (31.5 g, 160.0 mmol) and was used for the next step without purification.

Workup

  1. customwas reduced with high vacuum rotation evaporator at 65° C
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with water
  4. extractionThe combined water phases were extracted with dichloromethane
  5. washThe combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0805324ccfb84f8594aa88e035e14cd8
Source dataset
uspto-grants-2013_10
Patent number
US08557776B2

Reaction notes

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