Triethylamine → 3-(4-(2-Tert-butylphenyl)piperazin-1-yl)-3-oxopropanenitrile

HRID 534918Notes

Reaction equation

HRID 534918 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[C:17]([CH2:19][C:20](O)=[O:21])#[N:18].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:20](=[O:21])[CH2:19][C:17]#[N:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 469416591-(2-Tert-butylphenyl)piperazine

Product 1

HCID 667511633-(4-(2-Tert-butylphenyl)piperazin-1-yl)-3-oxopropanenitrileYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of provide 1-(2-tert-butylphenyl)piperazine (0.203 g, 0.69 mmol), 2-cyanoacetic acid (0.065 g, 0.77 mmol) and triethylamine (0.279 g, 2.76 mmol) in methylene chloride (5.0 mL) was added bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.202 g, 0.77 mmol) at room temperature. After 2.5 h the reaction mixture was diluted with methylene chloride (10.0 mL), washed with water (20.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50% ethyl acetate/heptanes) to provide 3-(4-(2-tert-butylphenyl)piperazin-1-yl)-3-oxopropanenitrile (0.114 g, 58%) as an off-white solid, mp 163-164° C.

Workup

  1. washwashed with water (20.0 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, 50% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-5edb6740382d493e85b3f95285e25da9
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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