Water → Ethyl 4-benzylhomopiperazine-1-carboxylate

HRID 704388Notes

Reaction equation

HRID 704388 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCCC1>[CH2:19]([N:10]1[CH2:11][CH2:12][CH2:13][N:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:9]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15289249Ethyl 1,4-diazepane-1-carboxylate

Product 1

HCID 54118699Ethyl 4-benzylhomopiperazine-1-carboxylateYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (0.80 g) was added to a solution of 0.86 g of ethyl 1-homopiperazinecarboxylate and 0.90 g of benzylbromide in 5 ml of tetrahydrofuran, and the mixture was refluxed for 4 hours. Thereafter, water was added, and the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. Elution with a hexane-ethyl acetate (2:1) mixture gave 1.06 g of ethyl 4-benzylhomopiperazine-1-carboxylate.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washElution with a hexane-ethyl acetate (2:1) mixture

Sources & evidence

ORD record
ord-44dc4856693543f0ab0196b548d7723b
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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