Diethylamine → HCID 23149973, compound

HRID 1670764Notes

Reaction equation

HRID 1670764 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7]Br.[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12].[C:16](=[O:19])([O-])[O-].[K+].[K+]>C(#N)C>[Cl:10][C:5]1[CH:4]=[CH:3][C:2]([C:16]2([OH:19])[CH2:15][CH2:14][NH:13][CH2:11][CH2:12]2)=[CH:9][C:6]=1[CH2:7][N:13]([CH2:14][CH3:15])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzene

Product 1

HCID 23149973HCID 23149973, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-2-chlorobenzylbromide (1.3 g) was dissolved in acetonitrile (30 ml). Diethylamine (334 mg) and potassium carbonate (2 g) were added thereto, and the mixture was heated under reflux for 1 hr. After completion of the reaction, the reaction mixture was filtrated, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (2:1-1:2)) to give a white solid. By a similar operation as in Starting Material Synthetic Example 45, 4-{4-chloro-3-[(diethylamino)methyl]phenyl}piperidin-4-ol (610 mg, yield 46%) was obtained from this white solid (1.24 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtrated
  5. concentrationthe filtrate was concentrated
  6. customThe obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (2:1-1:2))
  7. customto give a white solid

Sources & evidence

ORD record
ord-63e9b63a291441498db3d602dcd25d0a
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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