Benzyl Chloride → 1-Benzyl-1,4-diazepane

HRID 2119343Notes

Reaction equation

HRID 2119343 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl.N1CCCNCC1.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([N:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 68163Hexahydro-1,4-diazepineHCID 23441047Homopiperazine dihydrochloride

Product 1

HCID 2283651-Benzyl-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 101 mg of homopiperazine, 175 mg of homopiperazine dihydrochloride, 3 mL of ethanol was heated to 70° C. into a solution. 0.115 mL of benzyl chloride was added and the mixture was stirred at 70° C. for 3 hours. After cooling to room temperature, ethanol was removed under reduced pressure, and 20 mL of aqueous 2N sodium hydroxide solution was added to the solution, which was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined, washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 1-benzyihomopiperazine.

Workup

  1. temperatureAfter cooling to room temperature
  2. customethanol was removed under reduced pressure, and 20 mL of aqueous 2N sodium hydroxide solution
  3. additionwas added to the solution, which
  4. extractionwas extracted with 20 mL×2 of ethyl acetate
  5. washwashed with 20 mL of saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-96396319e79d43c4b618c653f72517a8
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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