Triethylamine → 1-(1-Oxo-2-propenyl)-4-(phenylmethyl)piperazine

HRID 1085410Notes

Reaction equation

HRID 1085410 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(OCC)C>[O:4]=[C:1]([N:16]1[CH2:17][CH2:18][N:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14][CH2:15]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 759941-Benzylpiperazine

Product 1

HCID 150562931-(1-Oxo-2-propenyl)-4-(phenylmethyl)piperazineYield 13%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of acryloyl chloride (4.52 g, 0.05 mole) in 25 ml of ethyl ether was added to a cold solution of 1-benzylpiperazine (8.8 g, 0.05 mole) and triethylamine (30 ml, 0.20 mole) in 500 ml of ethyl ether. A white precipitate formed. The reaction mixture was stirred overnight, filtered and the precipitate washed well with ethyl ether. The solvent and triethylamine were removed and the product chromatographed on silica, eluting with ethyl acetate/hexane [30:70 (v/v)] to yield 1.5 g of the title compound. The structure was confirmed by NMR.

Workup

  1. customA white precipitate formed
  2. filtrationfiltered
  3. washthe precipitate washed well with ethyl ether
  4. customThe solvent and triethylamine were removed
  5. customthe product chromatographed on silica
  6. washeluting with ethyl acetate/hexane [30:70 (v/v)]

Sources & evidence

ORD record
ord-821ab793c54147ef9c2bc4e35e2863bd
Source dataset
uspto-grants-1991_04
Patent number
US05010080

Reaction notes

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