N,N-Dimethylethylenediamine → HCID 53640412, compound

HRID 267812Notes

Reaction equation

HRID 267812 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22]>C1(C)C=CC=CC=1>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH:22][C:14](=[O:15])[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)=[CH:8][CH:9]=1)[CH3:17]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 54412737HCID 54412737, compound

Product 1

HCID 53640412HCID 53640412, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 6 g of α-[p-(1-cyclohexenyl)-phenyl]-propionic acid chloride in 10 ml of toluene is added dropwise with stirring at room temperature to a solution of 6 g of β-dimethylamino-ethylamine in 40 ml of toluene. The reaction mixture is stirred for two hours, then extracted with 2N hydrochloric acid, the hydrochloric acid solution washed with ethyl acetate and rendered alkaline with 4N sodium hydroxide solution. The batch is extracted with ethyl acetate, washed with water, dried over sodium sulphate and evaporated in vacuo. The solid residue is recrystallized from methylene chloride and petroleum ether to yield N-(β-dimethylamino-ethyl)-α-[p-(1-cyclohexenyl)-phenyl]-propionic acid amide of the formula ##SPC13##

Workup

  1. extractionextracted with 2N hydrochloric acid
  2. washthe hydrochloric acid solution washed with ethyl acetate
  3. extractionThe batch is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe solid residue is recrystallized from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-629987160c154fcead44eb4696b0828c
Source dataset
uspto-grants-1976_03
Patent number
US03944589

Reaction notes

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