HCID 21396418, compound → HCID 21396395, compound

HRID 1439762Notes

Reaction equation

HRID 1439762 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]([CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])[CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].[CH3:26][Mg]I>C(OCC)C>[CH2:15]([N:12]([CH2:13][CH3:14])[CH2:11][CH2:10][N:9]([CH2:17][C:18]([OH:19])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:26])[C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:16]

Participants

4

Reactant 2

HCID 21396418HCID 21396418, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21396395HCID 21396395, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.10 mole of 2-[N-(2,5-dichlorophenyl)-N-(β-diethylaminoethyl)amino]acetophenone in 200 ml of dry diethylether is added to a solution of 0.10 mole of methylmagnesium iodide in 500 ml of dry diethylether maintained at a temperature of from 0° to -5° C under nitrogen atmosphere. Thirty minutes after the addition the reaction mixture is washed with ice cold aqueous 2M ammonium chloride, dried over sodium sulfate, filtered and evaporated to give N-(β-diethylaminoethyl)-N-(β-hydroxy-β-phenylpropyl)-2,5-dichloroaniline.

Workup

  1. temperaturemaintained at a temperature of from 0° to -5° C under nitrogen atmosphere
  2. additionThirty minutes after the addition the reaction mixture
  3. washis washed with ice cold aqueous 2M ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1b02066839fb47c5a777f647b86f7089
Source dataset
uspto-grants-1977_11
Patent number
US04060630

Reaction notes

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