Benzyl Chloride → HCID 15517254, compound

HRID 981902Notes

Reaction equation

HRID 981902 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH2:23]([NH:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 775752,2-Diphenylethylamine

Product 1

HCID 15517254HCID 15517254, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,2-diphenyl ethyl amine (10.0 g, 0.051 mol) and triethyl amine (20.5 g, 0.203 mol) in 200 mL tetrahydrofuran was added a solution of benzyl chloride (7.1 g, 0.056 mol) in 100 mL tetrahydrofuran. The reaction mixture was heated to reflux for 48 hours, then cooled to room temperature and concentrated in vacuo. The residue was taken up in 300 mL chloroform and washed with 3×100 mL water. The organic layer was then stirred with 100 mL 2N NaOH solution for 30 minutes. The layers were separated and the aqueous layer was extracted further with 2×100 mL chloroform. The chloroform layers were combined, dried over sodium sulfate, filtered, and concentrated under vacuum. The resulting oil was further purified by chromatography, eluting with hexane/ethyl acetate. 5.8 g of a clear oil was isolated which was characterized by analytical and spectroscopic properties as the hydrochloride salt, mp 250-253° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 hours
  3. concentrationconcentrated in vacuo
  4. washwashed with 3×100 mL water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted further with 2×100 mL chloroform
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe resulting oil was further purified by chromatography
  11. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-baaf29b27c2a4b95a3c40f6390c0d503
Source dataset
uspto-grants-1991_02
Patent number
US04994465

Reaction notes

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