1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 21469814, compound

HRID 2295156Notes

Reaction equation

HRID 2295156 reaction equation
[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24]Cl)[CH3:21].[OH-].[K+]>CC(C)=O>[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][N:4]([C:1](=[O:3])[CH3:2])[C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:6]=1)[CH3:21]

Participants

5

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium HydroxideHCID 228532N-(4-benzoylphenyl)acetamide

Product 1

HCID 21469814HCID 21469814, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine N-acetyl-4-aminobenzophenone (4.0 g, 16.7 mmol), 2-diethylaminoethyl chloride hydrochloride (3.97 g, 23.1 mmol), and powdered potassium hydroxide (2.81 g, 50.1 mmol) in acetone (30 mL). Heat to reflux. After 2 hours, cool and decant the solvent. Evaporate the solvent in vacuo to give a residue. Partition the residue between water and ethyl acetate. Separate the organic layer and extract with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf =0.0-0.14 (streaks on silica gel, ethyl acetate).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customdecant the solvent
  4. customEvaporate the solvent in vacuo
  5. customto give a residue
  6. customPartition the residue between water and ethyl acetate
  7. customSeparate the organic layer
  8. extractionextract with water
  9. dry with materialDry the organic layer over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo

Sources & evidence

ORD record
ord-12d66c0358ba4efbb5e1d0236169502a
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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