Benzoyl chloride → HCID 22341479, compound

HRID 584889Notes

Reaction equation

HRID 584889 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CN.C1COCC1.[CH2:16]([N:18](CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:18]([CH3:16])[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 70217363-Bromophenethylamine

Product 1

HCID 22341479HCID 22341479, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9 g (45 mmol) of (3-bromo benzyl)methylamine, 90 ml of THF and 6.9 ml (50 mmol) of triethylamine are introduced into a round-bottomed flask under a stream of nitrogen. 5.7 ml (50 mmol) of benzoyl chloride are added dropwise and the mixture is stirred for one hour. The reaction medium is poured into water and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluded with a mixture of ethyl acetate and heptane (15/85). After evaporation of the solvents, 13.7 g (64%) of the expected product are collected.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic phase is separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. additioneluded with a mixture of ethyl acetate and heptane (15/85)
  9. customAfter evaporation of the solvents, 13.7 g (64%) of the expected product
  10. customare collected

Sources & evidence

ORD record
ord-e6c31afa94f94c65bf537859a3cb9ecd
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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