Triethylamine → 4-Benzyloxycarbonyl-3-dimethylaminopropylpiperazine

HRID 342502Notes

Reaction equation

HRID 342502 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29]Cl>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 541555964-Benzyloxycarbonyl-3-dimethylaminopropylpiperazineYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension mixture of benzyloxycarbonylpiperazine (14.529, 65.9 mmol), 3-dimethyl-aminopropyl chloride hydrochloride (15.63 g, 98.9 mmol), and triethylamine (20.29, 200 mmol) in ethanol (100 ml) was refluxed for 14 h. Then 3-dimethylaminopropyl chloride hydrochloride (6.32 g, 40 mmol), and triethylamine (11.3 ml, 80 mmol) was added to the reaction mixture and continued to reflux for 24 h. The solvent was evaporated and the residue was extracted with ethyl actate. The extract was washed with water, dried (MgSO4), and concentrated to give 12.65 g of brown viscous oil, which was purified by column chromatography on silica gel (ammonium hydroxide aqueous solution/methanol/dichloromethane: 1/10/100) to give 2.21 g of brown clear oil.

Workup

  1. temperaturewas refluxed for 14 h
  2. temperatureto reflux for 24 h
  3. customThe solvent was evaporated
  4. extractionthe residue was extracted with ethyl actate
  5. washThe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-203a6a6f5f9d44fcb42038d21c226a2a
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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