Diethylamine → HCID 15057236, compound

HRID 2073720Notes

Reaction equation

HRID 2073720 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Br[CH2:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)=[O:9]>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Product 1

HCID 15057236HCID 15057236, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 38.1 g (0.52 mol) of diethylamine in 80 mL of toluene and cooled in an ice bath to 0° C. add dropwise a solution of 65.0 g (0.26 mol) of 2-bromoacetonaphthone in 300 mL of toluene. Stir the reaction mixture overnight. Monitor the progress of the reaction by thin-layer chromatography on silica gel (ethyl acetate:hexane, 1:1). Extract the reaction mixture with 3×150 mL of 3N HCl. Adjust the pH of the combined aqueous layers to pH=10 with 50% sodium hydroxide then extract with 3×150 mL of methylene chloride. Combine the extracts and dry over sodium sulfate. Remove the solvent in vacuo, and chromatograph the resultant oil on 2200 g of silica gel, eluting initially with methylene chloride and later with ethyl acetate. Combine the fractions containing product and remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (ethyl acetate:hexane, 1:1)
  2. extractionExtract the reaction mixture with 3×150 mL of 3N HCl
  3. extractionthen extract with 3×150 mL of methylene chloride
  4. dry with materialdry over sodium sulfate
  5. customRemove the solvent in vacuo, and chromatograph the resultant oil on 2200 g of silica gel
  6. washeluting initially with methylene chloride and later with ethyl acetate
  7. additioncontaining product
  8. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-04e74c6c119b4debadb4572db8dd1e29
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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