Triethylamine → (R)-N-benzoyl-3-methyl-N'-(2-cyano-acetyl)piperazine

HRID 7597

Reaction equation

HRID 7597 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C.[C:23]([CH2:25][C:26]([OH:28])=O)#[N:24].[C:29]([N:37]1[CH2:42][CH2:41][NH:40][C@H:39]([CH3:43])[CH2:38]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[C:29]([N:37]1[CH2:42][CH2:41][N:40]([C:26](=[O:28])[CH2:25][C:23]#[N:24])[C@H:39]([CH3:43])[CH2:38]1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 7578227(R)-1-Benzoyl-3-methylpiperazine

Product 1

HCID 58630501(R)-N-benzoyl-3-methyl-N'-(2-cyano-acetyl)piperazineYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DCC (2.43 g) and triethylamine (5 ml) were added into a solution of cyanoacetic acid (1.00 g) and (R)-N-benzoyl-3-methylpiperazine (2.84 g) in THF (50 ml). After reaction stirred at room temperature for 12 hours, solvents were removed under vacuum to give a residue which was purified by silica gel column chromatography to afford 3 g of (R)-N-benzoyl-3-methyl-N′-(2-cyano-acetyl)piperazine. MS m/z: (M+H)+ calcd for C15H18N3O2 272.14, found 272.17. HPLC retention time: 0.93 minutes (column H).

Workup

  1. customAfter reaction
  2. customsolvents were removed under vacuum
  3. customto give a residue which
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a0df95c9b4b498e9f87abb23dd872c0
Source dataset
uspto-grants-2006_08
Patent number
US07087610B2

Linked notes

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