Dimethylamine → (Z)-3-(4-chlorophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine oxalate

HRID 1649545Notes

Reaction equation

HRID 1649545 reaction equation
Cl[CH2:2][CH:3]=[C:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.[CH3:18][NH:19][CH3:20].O.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl.CC(C)=O>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[Cl:17][C:14]1[CH:15]=[CH:16][C:11](/[C:4](/[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)=[CH:3]/[CH2:2][N:19]([CH3:20])[CH3:18])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 971Oxalic AcidHCID 544100933-Chloro-1-(4-chlorophenyl)-1-(3-pyridyl)-1-propene

Product 1

HCID 20478943(Z)-3-(4-chlorophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine oxalateYield 35%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of crude 3-chloro-1-(4-chlorophenyl)-1-(3-pyridyl)-1-propene (40 mmol) was added to dimethylamine (18.0 g, 400 mmol) in 25 ml methylene chloride at 10° C. After stirring at room temperature for 1.5 h 25 ml water were added, the phases separated and the solvent removed from the organic phase. The residue was taken up in ether and extracted with dilute hydrochloric acid to pH 4.5. The aqueous phase was made alkaline, extracted with ether and the solvent removed. The residual oil (6.8 g) was dissolved in acetone and one equivalent of oxalic acid in acetone was added. The precipitated oxalate was recrystallized twice from ethanol to give 5.1 g (35%) of pure product mainly (95%) containing the Z-isomer. M.p. 164°-168° C.

Workup

  1. additionwere added
  2. customthe phases separated
  3. customthe solvent removed from the organic phase
  4. extractionextracted with dilute hydrochloric acid to pH 4.5
  5. extractionextracted with ether
  6. customthe solvent removed
  7. dissolutionThe residual oil (6.8 g) was dissolved in acetone
  8. customThe precipitated oxalate was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-9282b763ad8b42c6a45494929f6391ac
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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