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

HRID 1032647Notes

Reaction equation

HRID 1032647 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 chromatrographed 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. washeluting with ethyl acetate/hexane [30:70(v/v)]

Sources & evidence

ORD record
ord-a491197c42204be1af351d49df346060
Source dataset
uspto-grants-1990_09
Patent number
US04959364

Reaction notes

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