Hydrochloric Acid → HCID 21469814, compound

HRID 1938653Notes

Reaction equation

HRID 1938653 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+].Cl>CC(C)=O.CO.C(OCC)(=O)C.C(OCC)(=O)C.O.COC(C)(C)C>[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

10

Reactant 4

HCID 313Hydrochloric AcidHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium HydroxideHCID 228532N-(4-benzoylphenyl)acetamide

Product 1

HCID 21469814HCID 21469814, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolventHCID 21584119Ethylacetate methanolSolvent2×

Procedure

Combine N-acetyl-4-aminobenzophenone (250 g, 1.05 mol), 2-diethylaminoethyl chloride hydrochloride (207.5 g, 1.20 mol), and 85% potassium hydroxide (140 g, 2.12 mol) in acetone (3 L). Heat to reflux. After 2 hours, cool and filter. Evaporate the filtrate in vacuo to give a residue. Combine the residue and t-butyl methyl ether (1 L) and water (2 L). Add aqueous 1M hydrochloric acid solution until the pH is about 2.5. Separate the aqueous layer and extract several times with t-butyl methyl ether. Adjust the pH of the aqueous layer to 10 using aqueous 50% sodium hydroxide solution. Extract the aqueous layer twice with dichloromethane. Dry the combined dichlormethane layers over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 5/95 methanol/ethyl acetate, 10/90 methanol/ethyl acetate to give the title compound: Rf =0.36 (silica gel, 2/8/0.1 methanol/ethyl acetate/triethylamine).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. filtrationfilter
  4. customEvaporate the filtrate in vacuo
  5. customto give a residue
  6. customSeparate the aqueous layer
  7. extractionextract several times with t-butyl methyl ether
  8. extractionExtract the aqueous layer twice with dichloromethane
  9. dry with materialDry the combined dichlormethane layers over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo
  12. customto give a residue

Sources & evidence

ORD record
ord-b4c7df4ea8f8456788095c141001ec62
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

Loading…