Dibenzylamine → HCID 57516721, compound

HRID 629214Notes

Reaction equation

HRID 629214 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C(#N)C>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 11430Potassium CarbonateHCID 21642Bromopinacolone

Product 1

HCID 57516721HCID 57516721, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

(2.15 ml, 16.8 mmol) Dibenzylamine was dissolved in acetonitrile (30 ml). Potassium carbonate (2.3 g, 16.8 mmol, 1.5 equiv.) and 1-bromo-3,3-dimethylbutan-2-one (1.5 ml, 11.2 mmol, 1.0 equiv.) were added and the mixture was stirred for 16 hours at 90° C. The reaction mixture was extracted with sat. NaHCO3-solution and two times EtOAc. The organic layers were extracted with water, dryed over Na2SO4, filtered and evaporated to dryness. The crude material was purified by flash chromatography on silica gel (70 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 1-(dibenzylamino)-3,3-dimethylbutan-2-one (1.6 g, 48.5% yield) was obtained as a yellow oil, MS: m/e=296.3 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with sat. NaHCO3-solution and two times EtOAc
  2. extractionThe organic layers were extracted with water
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude material was purified by flash chromatography on silica gel (70 gr, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record
ord-00320610162d4ed7916861907b6a2e7d
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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