Chloroacetonitrile → 2-(4-Benzylpiperazin-1-yl)acetonitrile

HRID 7598

Reaction equation

HRID 7598 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH2:5]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.CCN(CC)CC>[CH2:5]([N:12]1[CH2:17][CH2:16][N:15]([CH2:2][C:3]#[N:4])[CH2:14][CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 759941-Benzylpiperazine

Product 1

HCID 38557212-(4-Benzylpiperazin-1-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

An excess of chloroacetonitrile (7 ml) was added in to a solution of benzylpiperazine (2 g, 10.5 mmol) in THF (100 ml) and Et3N (10 ml). The reaction was stirred for 10 hours before quenched with saturated aqueous NaHCO3 (100 ml). The aqueous phase was extracted with EtOAc (3×100 ml). The combined organic layer was dried over MgSO4 and concentrated to a residue, which was used in the further reactions without any purification.

Workup

  1. custombefore quenched with saturated aqueous NaHCO3 (100 ml)
  2. extractionThe aqueous phase was extracted with EtOAc (3×100 ml)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. concentrationconcentrated to a residue, which
  5. customwas used in the further reactions without any purification

Sources & evidence

ORD record
ord-f3be17d383a14b1f9a00d9ceecf8569f
Source dataset
uspto-grants-2006_08
Patent number
US07087610B2

Linked notes

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